Fluoroalkoxybenzene derivatives having ether bond, liquid-crystal composition, and liquid-crystal display element

ABSTRACT

Liquid crystalline compounds superior in having an eminent dielectric anisotropy, being stable against environment and having improved miscibility with other liquid crystalline compounds, as well as a liquid crystal composition with driving-ability at a low voltage and responsibility at a high-speed comprising the compounds as a constituting component, and a liquid crystal display element comprising the composition are provided, said compounds are fluoroalkoxybenzene derivatives expressed by the general formula (1)                    
     wherein A 1 , A 2  and A 3  each independently denote trans-1,4-cyclohexylene,1,4-phenylene or so; B, B 2  and B 3  each independently denote a single bond, 1,2-ethylene or so; R denotes an alkyl group having 1 to 15 carbon atoms optionally substitutable with a halogen atom(s); Rf denotes a fluoroalkyl group having 1 to 3 carbon; k, m, and n each independently denote 0 or 1; with the proviso that when k=0 is a case, then one of B 1 , B 2  and B 3  is a methyleneoxy bond or so, and that when m+n≧1 is a case, then dependency of A 1 , A 2  and A 3  is partly restricted and content of Rf is partly limited when B 1  or/and B 2  and B 3  are all single bonds.

This application is a 371 application of PCT/JP98/04028 filed Sep. 8, 1998.

TECHNICAL FIELD

The present invention relates to a liquid crystalline compound and a liquid crystal composition. In more detail, the invention relates to a fluoroalkoxybenzene derivative having an ether linkage and being preferable as a component of liquid crystal composition, a liquid crystal composition comprising the derivative, and a liquid crystal display element fabricated by using the liquid crystal composition.

BACKGROUND ART

Liquid crystal display elements utilize optical anisotropy and dielectric anisotropy of liquid crystalline compounds. They are divided into modes such as twisted nematic (TN), super twisted nematic (STN), dynamic scattering (DS), guest-host (GH) and DAP type mode or so depending on their display modes on the electric optical effects, and also divided into driving modes such as static, time sharing addressing, active matrix and two-frequency addressing scheme.

Recently, particularly high quality display elements are required, and needs for display elements of active matrix types exemplified by a thin film transistor (TFT) type is increased. Furthermore, in order to improve response time against a change of an electric field or in order to lower a driving voltage, there are particularly required liquid crystal materials having higher dielectric anisotropy values (Δε) and lower viscosity values. Liquid crystal materials used in said liquid crystal, display elements are required to exhibit a liquid crystal phase at temperatures in a wide range and to be stable against heat, light, moisture, air, electric field and electromagnetic radiation or so. However, no compounds are found at present which satisfy such requirements by a single compound, and thus it is a current situation that a plurality, often as much of 20 or more, of liquid crystalline compounds are mixed and used. In particular, since there are recently many cases that liquid crystal display elements are used under such severe conditions as a quite low temperature or so, improvement in miscibility at a low temperature is also required.

Since TFT type liquid crystal display element needs a holding of electric charge stored between electrodes of pixels during a flame period, liquid crystal materials therefor are required to have a particularly high voltage holding ratio. Liquid crystalline compounds having fluorine atoms in their molecules have been used hitherto as liquid crystal materials which satisfy such requirements and have relatively high Δε.

For example, fluoroalkoxybenzene derivatives shown by the formulae (10) to (18)

wherein R denotes an alkyl group and Rf denotes a fluoroalkyl group, are now known.

However, compounds shown by the general formulae (10) or (11) which are disclosed in WO 94/26838 or DE 19528085 A1 have no or narrow liquid crystal temperature range, and furthermore their electric anisotropy values can never be said high enough.

As to compounds shown by the general formula (12) which are disclosed in Laid-open Japanese Patent Publication No. Hei 7-165656, their dielectric anisotropy values can also never be said high enough. Furthermore, compounds shown by the general formula (14) are disclosed in DE 4027840 A1, but there is no description about their electric characteristics. Furthermore, compounds shown by the general formulae (13), (15), (16) and (18) are disclosed in DE 4218614 A1, EP 640578 A1, DE 4223501 A1, DE 4222371 A1, WO 9213928 A1, DE 4142519 A1 and DE 4027840 A1 or so. But there is no description about their physical properties, so that it can never be said that the invention is disclosed.

In addition, compounds shown by (17) are disclosed without any information about electric characteristics in DE 4301700 A1, but said compounds are considered to have no sufficient Δε value because dipolar moments thereof are offset by fluoroalkoxy groups at both terminals of the compounds.

We the inventors have studied eagerly to solve the above-mentioned problems and found a novel compound having improved characteristics compared to the known liquid crystalline compounds, and have completed the present invention.

As is clear from the above-mentioned description, an object of the present invention is to provide a liquid crystalline compound of fluoroalkoxybenzene derivatives having ether bond, having in particular large Δε value, being excellent in miscibility with other liquid crystalline compounds, having a low viscosity and being stable chemically and physically, as well as a liquid crystal composition, and a liquid crystal display element comprising the compound.

DISCLOSURE OF THE INVENTION

Inventions to be claimed in the present application are as follows.

(1) A fluoroalkoxybenzene derivative expressed by the general formula (1)

wherein A₁, A₂ and A₃ each independently denote trans-1,4-cyclohexylene,1,4-phenylene in which one or more hydrogen atoms may optionally be substituted with a fluorine atom(s), 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or 1-sila-1,4-cyclohexylene; B₁, B₂ and B₃ each independently denote a single bond, 1,2-ethylene, 1,2-ethenylene, 1,2-ethynylene, oxymethylene, methyleneoxy, carbonyloxy or 1,4-butylene group; R denotes an alkyl group having 1 to 15 carbon atoms optionally substitutable with a halogen atom(s), wherein one or more non-adjacent ethylene groups may be replaced by 1,2-ethenylene group(s); Rf denotes a fluoroalkyl group having 1 to 3 carbon atoms substitutable with two or more fluorine atoms; k, m, and n each independently denote 0 or 1, with the proviso that when k=0 is a case, then one of B₁, B₂ and B₃ is a methyleneoxy or oxymethylene bond, and that when m+n≧1 is a case, then A₁ or/and A₂ and A₃ are not 1,4-phenylene at the same time, and further when A₁ or/and A₂ and A₃ are trans-1, 4-cyclohexylene or 1,4-phenylene and B₁ or/and B₂ and B₃ are all single bonds, then Rf is never C₂F₅, CH₂CF₃ or CH₂CF₂CF₃, and that when m+n=1 is a case, A₁ or A₂ and A₃ are trans-1, 4-cyclohexylene at the same time, B₁ or B₂ is a single bond and B₃ is 1,2-ethylene, then Rf is never CH₂CF₂CF₃.

(2) A compound recited in paragraph (1) above wherein k=1.

(3) A compound recited in paragraph (1) above wherein one of B₁, B₂ or B3 is a methyleneoxy or oxymethylene bond.

(4) A compound recited in paragraph (2) above wherein m=0, n=1, A₂ and A₃ are 1, 4-cyclohexylene, and B₂ and B₃ are single bonds.

(5) A compound recited in paragraph (2) above wherein m=0, n=1, A₂ is 1, 4-cyclohexylene, A₃ is 1, 4-cyclohexylene optionally substitutable with a fluorine atom(s), and B₂ and B₃ are both single bonds.

(6) A compound recited in paragraph (2) above wherein m+n=1, A₁ or A₂ and A₃ are both trans-1, 4-cyclohexylenes, B₁ or B₂ is 1, 2-ethylene, and B₃ is a single bond.

(7) A compound recited in paragraph (2) above wherein m+n=1, A₁ or A₂ and A₃ are both trans-1, 4-cyclohexylenes, B₁ or B₂ is a single bond, and B₃ is 1,2-ethylene.

(8) A compound recited in paragraph (2) above wherein m=n=1, and A₁ and A₂ are both trans-1, 4-cyclohexylenes.

(9) A compound recited in paragraph (8) above wherein m=n=1, A₁ and A₂ are both trans-1, 4-cyclohexylenes, A₃ is 1, 4-phenylene one or two hydrogen atoms of which may optionally be substituted with a fluorine atom(s), B₁ and B₃ are single bonds, and B₂ is 1,2-ethylene.

(10) A liquid crystal composition comprising at least one liquid crystalline compound recited in any one of paragraphs (1) to (9).

(11) A liquid crystal composition comprising, as a first component, at least one liquid crystalline compound recited in any one of paragraphs (1) to (9), and as a second component, at least one compound selected from the group of compounds expressed by any one of general formulae (2), (3), and (4)

wherein R₃ denotes an alkyl group having 1 to 10 carbon atoms in which alkyl group any optional non-adjacent ethylene group may be replaced by an oxygen atom or —CH═CH—, and any optional hydrogen atom may be substituted with a fluorine atom; Y₁ denotes a fluorine atom, a chlorine atom, OCF₃, OCF₂ H, CF₃, CF₂H, CFH₂, OCF₂CF₂H or OCF₂CFHCF₃; L₁ and L₂ each independently denote a hydrogen atom or a fluorine atom; Z₁ and Z₂ each independently denote 1,2-ethylene group, 1,4-butylene group, —COO—, —CF₂O—, —OCF₂—, —CH═CH—, or a single bond; ring B denotes trans-1,4-cyclohexylene, 1,3-dioxane-2,5-diyl or 1,4-phenylene any hydrogen atom of which may be substituted with a fluorine atom; and ring C denotes trans-1,4-cyclohexylene or 1,4-phenylene any hydrogen atom of which may be substituted with a fluorine atom.

(12) A liquid crystal composition comprising, as a first component, at least one liquid crystalline compound recited in any one of paragraphs (1) to (9), and as a second component, at least one compound selected from a group of compounds expressed by any one general formulae (5) and (6)

wherein R₄ and R₅ each independently denote an alkyl group having 1 to 10 carbon atoms in which alkyl group any optional non-adjacent methylene group may be replaced by an oxygen atom or —CH═CH— and any optional hydrogen atom of which may be substituted with a fluorine atom; Y₂ denotes —CN group or —C≡C—CN group; ring E denotes trans-1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; ring G denotes trans-1,4-cyclohexylene, 1,4-phenylene any hydrogen atom of which may be substituted with a fluorine atom or pyrimidine-2, 5-diyl; ring H denotes trans-1, 4-cyclohexylene or 1,4-phenylene; Z₃ denotes 1,2-ethylene group, —COO— or a single bond; L₃, L₄ and L₅ each independently denote a hydrogen atom or a fluorine atom, and b, c and d each independently denote 0 or 1.

(13) A liquid crystal composition comprising, as a first component, at least one liquid crystalline compound recited in any one of paragraphs (1) to (9), as a second component, at least one compound selected from the group of compounds expressed by any one of general formulae (2), (3), and (4) described above, and as a third component, at least one compound selected from a group of compounds expressed by any one of the general formulae (7), (8) and (9)

wherein R₆ and R₇ each independently denote an alkyl group having 1 to 10 carbon atoms in which alkyl group any optional non-adjacent methylene group may be replaced by an oxygen atom or —CH═CH— and any optional hydrogen atom of which may be substituted with a fluorine atom; I, J and K each independently denote trans-1,4- cyclohexylene, pyrimidine-2,5-diyl or 1,4-phenylene any hydrogen atom of which may be substituted with a fluorine atom; and Z₄ and Z₅ each independently denote —C≡C—, —COO—, —CH₂CH₂—, —CH═CH— or a single bond.

(14) A liquid crystal composition comprising, as a first component, at least one liquid crystalline compound recited in any one of paragraphs (1) to (9), as a second component, at least one compound selected from the group of compounds expressed by any one of general formulae (5) and (6) described above, and as a third component, at least one compound selected from a group of compounds expressed by any one of the general formulae (7), (8) and (9) described above.

(15) A liquid crystal composition comprising, as a first component, at least one liquid crystalline compound recited in any one of paragraphs (1) to (9), as a second component, at least one compound selected from the group of compounds expressed by any one of general formulae (2), (3), and (4) described above, as a third component, at least one compound selected from a group of compounds expressed by any one of the general formulae (5) and (6) described above, and as a fourth component, at least one compound selected from a group of compounds expressed by any one of the general formulae (7), (8) and (9) described above.

(16) A liquid crystal composition recited in any one of paragraph (10) to (15) wherein the liquid crystal composition further comprises one or more optically active compounds.

(17) A liquid crystal display element fabricated by using a liquid crystal composition recited in any one of paragraphs (10) to (15)

BEST MODE FOR CARRYING OUT THE INVENTION

Although the liquid crystalline compounds of the present invention are expressed by the general formula (1) as described above, the compounds expressed by the following formulae (1-1) to (1-71) can particularly be mentioned as preferable examples amongst of them.

In the above-mentioned formulae, R denotes an alkyl group, W denotes methyleneoxy or oxymethylene group, and Rf denotes a fluoroalkyl group having 1 to 3 carbon atoms in which two or more fluorine atoms are substituted.

Any of these compounds of the present invention have superior characteristics such as exhibiting particularly high dielectric anisotropy, high voltage holding ratio, low viscosity and good miscibility at a low temperature. In particular, two-ring or three-ring system compounds expressed by the formulae (1-1) to (1-26) exhibit high dielectric anisotropy and good miscibility at a low temperature. Therefore, by using liquid crystal compositions comprising these compounds, liquid crystal cells to be driven at a low voltage can be manufactured. Furthermore, four-ring system compounds expressed by the formulae (1-27) to (1-71) exhibit high dielectric anisotropy, and have eminently high clear point while have relatively low viscosity.

Therefore, by using liquid crystal compositions comprising these compounds, liquid crystal cells with wide display temperature range and being driven at low voltage can be manufactured.

Liquid crystalline compounds of the present invention expressed by the general formula (1) do not always exhibit liquid crystal phase. But they are effective when they are mixed with other liquid crystalline compounds, because any of them has a good miscibility with other liquid crystalline compounds and can give compositions without eminently lowered nematic phase temperature or reduced range thereof. Therefore, any of the liquid crystalline compounds expressed by the general formula (1) having such superior optical characteristics as described above can be an useful constitutional component of a liquid crystal composition, even though it does not exhibit a liquid crystal phase by itself.

Liquid crystal compositions of the present invention comprise, as the first component, at least one liquid crystalline compound expressed by the general formula (1).

Its content is preferably 0.1 to 99.9% by weight based on the amount of liquid crystal composition for developing excellent characteristics.

While the liquid crystal composition of the present invention may comprise only the first component described above, the composition in which at least one compound selected from the group consisting of the compound expressed by one of the general formulae (2), (3) and (4) described above (hereinafter referred to as second component A) and/or at least one compound selected from the group consisting of the compound expressed by the general formulae (5) or (6) described above hereinafter referred to as second component B) are mixed as second component in addition to the first component, or the compositions in which at least one compound selected from the group consisting of the compound expressed by one of the general (7), (8), and (9) described above are further mixed as a third component in addition to the first and second components are preferable. Besides, an optically active compound as another component, and a known compound may be mixed for the purpose of adjusting threshold voltage, temperature range of liquid crystal phase, optical anisotropy value (Δn), Δε and a viscosity.

Among the second component A described above, the compounds expressed by one of the following formulae (2-1) to (2-9) can be mentioned as preferable examples of the ones included in the general formula (2), the compounds of one of the following formulae (3-1) to (3-69) can be mentioned as preferable examples of the ones included in the general formula (3), and the compounds of one of the following formulae (4-1) to (4-24) can be mentioned as preferable examples of the ones included in the general formula as preferable examples of compounds included in the general formula (4), respectively.

wherein R₃ and Y₁ have the same meanings as described above.

Any of the compounds expressed by one of the general formulae (2) to (4) exhibit a positive Δε, are excellent in thermal stability and chemical stability, and are indispensable when liquid crystal composition for TFT (AM-LCD) of which a high reliability such as a high voltage holding ratio (large specific resistance) is required are produced.

While the amount of the compound to be used is suitably in the range of 1 to 99.9% by weight based on the total amount of liquid crystal when liquid crystal composition for TFT are produced, it is preferably 10 to 97% by weight and more desirably 40 to 95% by weight. In this case, liquid crystal composition may further comprise a compound expressed by one of the general formulae (7) to (9) for the purpose of adjusting viscosity.

While the compounds expressed by one of the general formulae (2) to (4) described above can be used when liquid crystal compositions for STN display mode or a TN mode are produced, the amount of the compound to be used is preferably less than 50% by weight based on the total amount of liquid crystal composition since this compound is small in its effect of lowering threshold voltage of the liquid crystal composition.

Next, among the second component B, the compounds of one of the formulae (5-1) to (5-40) can be mentioned as preferable examples of the ones included in the general formula (5), and the compounds of one of the formulae (6-1) to (6-3) can be mentioned as preferable examples of the ones included in the general formula (6), respectively.

wherein R₄, Y₂ and R₅ have the same meanings as described above.

Any of the compounds expressed by the general formulae (5) or (6) has a positive and large Δε value, and is used particularly for the purpose of lowering threshold voltage of liquid crystal compositions.

Also, the compounds are used for the purposes of improving the steepness of liquid crystal compositions for STN display mode or TN display mode including for the purposes of adjusting Δn and raising clearing point of liquid crystal compositions, and thus are indispensable particularly when liquid crystal compositions for STN display mode or TN display mode are produced.

Whereas the compounds can lower threshold voltage of liquid crystal compositions as their amount used is increased, the use of the compounds brings about increase of the viscosity.

Accordingly, it is advantageous to use the compounds in a large amount for driving display element at a lower so far as the viscosity of liquid crystal compositions satisfies required characteristics.

Under such circumstances, the amount of the compounds to be used is suitably in a range of 0.1 to 99.9% by weight, preferably 10 to 97% by weight, and more preferably 40 to 95% by weight, based on the total amount of liquid crystal composition when liquid crystal compositions for STN display mode or TN display mode are produced.

Among the third component described above, the compounds of one of the formulae (7-1) to (7-11) can be mentioned as preferable examples of the ones included in the general formula (7), the compounds of one of the formulae (8-1) to (8-18) can be mentioned as preferable examples of the ones included in the general formula (8), and compounds of one of the formulae (9-1) to (9-6) can be mentioned as preferable examples of compounds included in the general formula (9).

wherein R₆ and R₇have the same meanings as described above.

Any of the compounds expressed by one of the general formulae (7) to (9) has a small absolute value of Δε. Among them, the compounds of the general formula (7) are used for the purpose of adjusting viscosity or adjusting Δn of liquid crystal composition, and the compounds of the general formulae (8) and (9) are used for the purposes of widening nematic range by such a way of raising clearing point or adjusting Δn.

Whereas these compounds raise threshold voltage of the liquid crystal compositions as their amount used is increased, the use of compounds reduces the viscosity. Accordingly, it is desirable to use the compounds in a larger amount so far as the threshold voltage of liquid crystal compositions satisfies required values.

From such circumstances, the used amount of the compounds to be used is suitably less than 40% by weight and preferably less than 35% by weight based on the total amount of liquid crystal composition when liquid crystal composition for a TFT display mode are produced. On the other hand, when liquid crystal compositions for STN display mode or TN display mode are produced, the amount of use described above is suitably less than 70% by weight and preferably less than 60% by weight.

Among other components, an optically active compound is usually added to the liquid crystal compositions of the present invention for the purpose of inducing helical structure of liquid crystal compositions to adjust required twist angle and to prevent reverse twist, with the exception of specific cases, for instance, the case of liquid crystal compositions for OCB (Optically Compensated Birefringence) mode. While the optically active compound is widely selected from known compounds so far as the purposes described above can be achieved, the optically active compounds expressed by one of the following formulae (Op-1) to (Op-8) can preferably be mentioned.

Pitch length of the twist in liquid crystal compositions is adjusted by adding these optically active compounds. The twist pitch length is preferably adjusted in the range of 40 to 200 μm in the case of liquid crystal compositions for TFT or TN mode, preferably adjusted in the range of 60 to 20 μm in the case of the liquid crystal compositions for STN mode, and preferably adjusted in the range of 1.5 to 4 μm in the case of liquid crystal compositions for bistable TN mode, respectively. Further, in such cases, two or more kind of optically active compounds may be added for the purpose of adjusting the dependency of pitch length on temperature.

Liquid crystal compositions of the present invention can be prepared by methods that are conventional by themselves. For instance, the compositions are prepared by a method in which various components are dissolved in one another at a high temperature.

Further, the liquid crystal compositions of the present invention can be used as ones for a guest-host (GH) mode by adding a dichroic dye such as merocyanine type, styryl type, azo type, azomethine type, azoxy type, quinophthalone type, anthraquinone type or tetrazine type. Alternatively, the liquid crystal compositions may be used as NCAP which is prepared by the microencapsulation of a nematic liquid crystal, or as liquid crystal compositions for polymer dispersed liquid crystal display elements (PDLCD) represented by polymer network liquid crystal display elements (PNLCD) prepared by forming a polymer of three-dimensional reticulated structure in a liquid crystal. Still further, the liquid crystal compositions of the present invention can be used as ones for electrically controlled birefringence (ECB) mode or dynamic scattering (DS) mode.

As of nematic liquid crystal compositions comprising the compounds of and prepared by the present invention as described above are mentioned as Examples below.

In each of the following Composition Examples, compounds are designated by making the groups shown in each of columns of left side terminal group, bonding group, ring structure, and right side terminal group correspond to the symbols shown in the columns of symbol according to the definition shown in Table 1 below.

Compound No. appended to the compounds of the present invention in the following Composition Examples means that the compounds are the same as those shown in Examples described below and having the same appended Compound No.; and the content of compounds means % by weight unless otherwise specified. Further, data of characteristics of compositions in Composition Examples are indicated by T_(NI) (phase transition temperature of nematic phase-isotropic liquid, or clearing point), η(viscosity, determined at a temperature of 20.0° C.), Δn (optical anisotropy value, determined at a temperature of 25.0° C.), V_(th) (threshold voltage, determined at a temperature of 25.0° C.) and P (pitch, determined at a temperature of 25.0° C.). Abbreviations shown herein are defined as table 1. [Table 1]

TABLE 1 Method for designating compounds by using symbols R-(A₁)-Z_(1- . . . -Z) _(n)-(A_(n))-X 1) Left side terminal group R- Symbol C_(n)H_(2n+1)— n— C_(n)H_(2n+1)O— nO— C_(n)H_(2n+1)OC_(m)H_(2m)— nOm— CH₂═CH— v— CH₂═CHC_(n)H_(2n)— Vn— C_(n)H_(2n+1)CH═CHC_(m)H_(2m)— nVm— CH₂═CHC_(n)H_(2n)CH═CH— VnV— 2) Ring structure -(A1)-, -(An)- Symbol

B

B(F)

B(F,F)

H

Py

G

Ch 3) Bonding group -Z₁-, -Z_(n)- Symbol —C₂H₄— 2 —C₄H₈— 4 —COO— E —C≡C— T —CH═CH— V —CF₂O— CF2O —OCF₂— OCF2 —OCH₂— O1 —CH₂O— 1O 4) Right side terminal group -X Symbol —F —F —Cl —CL —CN —C —CF₃ —CF3 —OCF₃ —OCF3 —OCF₂H —OCF2H —C_(n)H_(2n+1) —n —OC_(n)H_(2n+1) —On —COOCH₃ —EMe —C_(n)H_(2n)CH═CH₂ —nV —C_(m)H_(2m)CH═CHC_(n)H_(2n+1) —mVn —CH═CF₂ —VFF —C_(n)H_(2n)CH═CF₂ —nVFF —CH═CHC_(n)H_(2n)F —VnF —CH═CH₂ —V —C≡C—CN —TC 5) Examples of designation Example 1 3-H2B(F,F)B(F)-F

Example 2 3-HB(F)TB-2

Example 3 1V2-BEB(F,F)-C

COMPOSITION EXAMPLE 1

101-HHB(F,F)-OCF3 (No. 153) 5.0% 1V2-BEB(F,F)-C 5.0% 3-HB-C 25.0%  1-BTB-3 5.0% 2-BTB-1 10.0%  3-HH-4 11.0%  3-HHB-1 11.0%  3-HHB-3 4.0% 3-H2BTB-2 4.0% 3-H2BTB-3 4.0% 3-H2BTB-4 4.0% 3-HB(F)TB-2 6.0% 3-HB(F)TB-3 6.0%

Characteristics of the composition were determined as follows:

TNI=87.5(° C.)

η=16.7(mPa.s)

Δn=0.161

Δε=8.1

Vth=1.92(V)

0.8 parts of an optically active compound expressed by the above-mentioned formula (Op-4) was added to 100 parts of the above-mentioned composition to obtain the secondary composition, which has the following determined pitch: P=1 μm.

COMPOSITION EXAMPLE 2

A liquid crystal composition comprising the following compounds in an amount shown below was prepared:

5-H10BB(F,F)-OCF3 (No. 239) 5.0% 201-BEB(F)-C 5.0% 301-BEB(F)-C 15.0%  401-BEB(F)-C 13.0%  501-BEB(F)-C 13.0%  2-HHB(F)-C 10.0%  3-HHB(F)-C 15.0%  3-HB(F)TB-2 4.0% 3-HB(F)TB-3 4.0% 3-HB(F)TB-4 4.0% 3-HHB-1 8.0% 3-HHB-01 4.0%

Characteristics of the composition were determined to be as follows:

TNI=87.8(° C.)

η=87.1(mPa.s)

Δn=0.148

Δε=30.7

Vth=0.88 (V)

COMPOSITION EXAMPLE 3

101-HHB(F,F)-OCF3 (No. 153) 5.0% 5-H10BB(F,F)-OCF3 (No. 239) 5.0% 5-PyB-F 4.0% 3-PyB(F)-F 4.0% 2-BB-C 5.0% 4-BB-C 4.0% 5-BB-C 5.0% 2-PyB-2 2.0% 3-PyB-2 2.0% 4-PyB-2 2.0% 6-PyB-05 3.0% 6-PyB-06 3.0% 6-PyB-07 3.0% 6-PyB-08 3.0% 3-PyBB-F 6.0% 4-PyBB-F 6.0% 3-HHB-1 6.0% 3-HHB-3 8.0% 2-H2BTB-3 4.0% 2-H2BTB-4 5.0% 3-H2BTB-2 5.0% 3-H2BTB-3 5.0% 3-H2BTB-4 5.0%

Characteristics of the composition were determined as follows:

TNI=87.6(° C.)

η=39.1(mPa.s)

Δn=0.188

Δε=6.9

Vth=2.18(V)

COMPOSITION EXAMPLE 4

101-HHB(F,F)-OCF3 (No. 153) 5.0% 101-HB(F,F)B(F,F)-OCF3 (No. 187) 5.0% 3-GB-C 10.0%  4-GB-C 10.0%  2-BEB-C 12.0%  3-BEB-C 4.0% 3-PyB(F)-F 6.0% 3-HEB-04 4.0% 4-HEB-02 6.0% 5-HEB-01 6.0% 3-HEB-02 5.0% 5-HEB-5 5.0% 5-HEB-5 5.0% 10-BEB-5 4.0% 3-HHB-1 6.0% 3-HHEBB-C 2.0% 3-HBEBB-C 2.0% 5-HBEBB-C 3.0%

COMPOSITION EXAMPLE 5

5-H10BB(F,F)-OCF3 (No. 239) 5.0% 3-HB-C 18.0%  7-HB-C 3.0% 101-HB-C 10.0%  3-HB(F)-C 10.0%  2-PyB-2 2.0% 3-PyB-2 2.0% 4-PyB-2 2.0% 101-HH-3 7.0% 2-BTB-01 7.0% 3-HHB-1 7.0% 3-HHB-F 4.0% 3-HHB-01 4.0% 3-HHB-3 6.0% 3-H2BTB-2 3.0% 3-H2BTB-3 3.0% 2-PyBH-3 4.0% 3-PyBB-2 3.0%

Characteristics of the composition were determined as follows:

TNI=74.8(° C.)

η=21.0(mPa.s)

Δn=0.139

Δε=8.4

Vth=1.70(V)

COMPOSITION EXAMPLE 6

101-HHB(F,F)-OCF3 (No. 153) 3.0% 5-H10BB(F,F)-OCF3 (No. 239) 3.0% 201-BEB(F)-C 5.0% 301-BEB(F)-C 12.0%  501-BEB(F)-C 4.0% 1V2-BEB(F,F)-C 10.0%  3-HH-EMe 10.0%  3-HB-02 18.0%  7-HEB-F 2.0% 3-HHEB-F 2.0% 5-HHEB-F 2.0% 3-HBEB-F 4.0% 201-HBEB(F)-C 2.0% 3-HB(F)EB(F)-C 2.0% 3-HBEB(F,F)-C 2.0% 3-HB-F 4.0% 3-HHB-0 1.0% 3-HHB-3 7.0% 2-HEBEB-F 2.0% 2-HEBEB-1 2.0%

Characteristics of the composition were determined as follows:

TNI=72.2(° C.)

η=38.9(mPa.s)

Δn=0.115

Δε=24.3

Vth=0.98(V)

COMPOSITION EXAMPLE 7

101-HHB(F,F)-OCF3 (No. 153) 4.0% 5-H10BB(F,F)-OCF3 (No. 239) 4.0% 201-BEB(F)-C 5.0% 301-BEB(F)-C 12.0% 501-BEB(F)-C 4.0% 1V2-BEB(F,F)-C 14.0%  3-HB-02 10.0%  3-HH-4 3.0% 3-HHB-F 3.0% 3-HHB-1 2.0% 3-HHB-01 4.0% 3-HBEB-F 4.0% 3-HHEB-F 7.0% 5-HHEB-F 7.0% 3-H2BTB-2 4.0% 3-H2BTB-3 4.0% 3-H2BTB-4 4.0% 3-HB(F)TB-2 5.0%

Characteristics of the composition were determined as follows:

TNI=85.7(° C.)

η=43.6(mPa.s)

Δn=0.141

Δε=27.9

Vth=1.01(V)

COMPOSITION EXAMPLE 8

101-HHB(F,F)-OCF3 (No. 153) 3.0% 5-H10BB(F,F)-OCF3 (No. 239) 3.0% 2-BEB-C 12.0%  3-BEB-C 4.0% 4-BEB-C 6.0% 3-HB-C 28.0%  3-HEB-04 12.0%  4-HEB-02 8.0% 5-HEB-01 5.0% 3-HEB-02 6.0% 5-HEB-02 5.0% 3-HHB-1 4.0% 3-HHB-01 4.0%

Characteristics of the composition were determined as follows:

TNI=60.2(° C.)

η=28.7(mPa.s)

Δn=0.111

Δε=10.7

Vth=1.30(V)

COMPOSITION EXAMPLE 9

101-HHB(F,F)-OCF3 (No. 153) 5.0% 2-BEB-C 10.0%  5-BB-C 12.0%  7-BB-C 7.0% 1-BTB-3 7.0% 2-BTB-1 10.0%  10-BEB-2 10.0%  10-BEB-5 12.0%  2-HHB-1 4.0% 3-HHB-F 4.0% 3-HHB-1 7.0% 3-HHB-01 4.0% 3-HHB-3 8.0%

Characteristics of the composition were determined as follows:

TNI=62.9(° C.)

η=22.2(mPa.s)

Δn=0.160

Δε=7.5

Vth=1.69(V)

COMPOSITION EXAMPLE 10

101-HHB(F,F)-OCF3 (No. 153) 5.0% 5-H10BB(F,F)-OCF3 (No. 239) 5.0% 101-HB(F,F)B(F,F)-OCF3 (No. 187) 5.0% 101-HB(F)B(F,F)-OCF3 (No. 199) 5.0% 2-HB-C 5.0% 3-HB-C 12.0%  3-HB-02 15.0%  2-BTB-1 3.0% 3-HHB-1 8.0% 3-HHB-F 4.0% 3-HHB-01 5.0% 3-HHB-3 9.0% 3-HHEB-F 4.0% 2-HHB(F)-F 3.0% 3-HHB(F)-F 7.0% 3-HHB(F,F)-F 5.0%

COMPOSITION EXAMPLE 11

5-H10BB(F,F)-OCF3 (No. 239) 5.0% 3-BEB(D)-C 8.0% 3-HB-C 8.0% V-HB-C 8.0% 1V-HB-C 8.0% 3-HB-02 3.0% 3-HH-2V 14.0%  3-HH-2V1 7.0% V2-HHB-1 15.0%  3-HHB-1 5.0% 3-HHEB-F 2.0% 3-H2BTB-2 6.0% 3-H2BTB-3 6.0% 3-H2BTB-4 5.0%

Characteristics of the composition were determined as follows:

TNI=95.8(° C.)

η=19.3(mPa.s)

Δn=0.135

Δε=8.7

Vth=2.12(V)

COMPOSITION EXAMPLE 12

101-HHB(F,F)-OCF3 (No. 153) 3.0% 5-H10BB(F,F)-OCF3 (No. 239) 3.0% V2-HB-C 12.0%  1V2-HB-C 12.0%  3-HB-C 15.0%  3-HB[1D,2D,3D]-C 9.0% 3-HB(F)-C 5.0% 2-BTB-1 2.0% 3-HH-4 8.0% 3-HH-VFF 6.0% 2-H[1D,2D,3D]HB-C 3.0% 3-HHB-C 6.0% 3-HB(F)TB-2 2.0% 3-H2BTB-2 5.0% 3-H2BTB-3 5.0% 3-H2BTB-4 4.0%

Characteristics of the composition were determined as follows:

TNI=82.4(° C.)

η=20.7(mPa.s)

Δn=0.145

Δε=9.3

Vth=1.78(V)

COMPOSITION EXAMPLE 13

101-HHB(F,F)-OCF3 (No. 153) 5.0% 5-H10BB(F,F)-OCF3 (No. 239) 5.0% 5-BTB(F)TB-3 10.0%  V2-HB-TC 10.0%  3-HB-TC 10.0%  3-HB-C 10.0%  5-HB-C 7.0% 5-BB-C 3.0% 2-BTB-1 10.0%  2-BTB-01 5.0% 3-HH-4 5.0% 3-HHB-1 5.0% 3-HHB-3 6.0% 3-H2BTB-2 3.0% 3-H2BTB-3 3.0% 3-HB(F)TB-2 3.0%

Characteristics of the composition were determined as follows:

TNI=100.1(° C.)

η=19.4(mPa.s)

Δn=0.204

Δε=8.1

Vth=1.93(V)

COMPOSITION EXAMPLE 14

101-HHB(F,F)-OCF3 (No. 153) 5.0% 2-HHB(F)-F 17.0%  3-HHB(F)-F 17.0%  5-HHB(F)-F 16.0%  2-H2HB(F)-F 10.0%  3-H2HB(F)-F 5.0% 5-H2HB(F)-F 10.0%  2-HBB(F)-F 6.0% 3-HBB(F)-F 6.0% 5-HBB(F)-F 8.0%

Characteristics of the composition were determined as follows:

TNI=98.8(° C.)

ηn=27.0(mPa.s)

Δn=0.090

Δε=5.7

Vth=2.11((V)

0.3 parts of an optically active compound expressed by the above-mentioned formula (Op-8) was added to 100 parts of the above-mentioned composition to obtain the secondary composition, which has the following determined pitch: P=79 μm

COMPOSITION EXAMPLE 15

101-HHB(F,F)-OCF3 (No. 153) 5.0% 5-H10BB(F,F)-OCF3 (No. 239) 5.0% 101-HB(F,F)B(F,F)-OCF3 (No. 187) 5.0% 101-HB(F)B(F,F)-OCF3 (No. 199) 5.0% 7-HB(F,F)-F 3.0% 3-HB-02 7.0% 2-HHB(F)-F 10.0%  3-HHB(F)-F 10.0%  2-HBB(F)-F 9.0% 3-HBB(F)-F 9.0% 5-HBB(F)-F 6.0% 2-HBB-F 4.0% 3-HBB-F 4.0% 5-HBB-F 3.0% 3-HBB(F,F)-F 5.0% 5-HBB(F,F)-F 10.0% 

COMPOSITION EXAMPLE 16

5-H10BB(F,F)-OCF3 (No. 239) 5.0% 3-HB-CL 10.0%  5-HB-CL 4.0% 7-HB-CL 4.0% 101-HH-5 5.0% 2-HBB(F)-F 8.0% 3-HBB(F)-F 8.0% 5-HBB(F)-F 9.0% 4-HHB-CL 8.0% 5-HHB-CL 8.0% 3-H2HB(F)-CL 4.0% 3-HBB(F,F)-F 10.0%  5-H2BB(F,F)-F 9.0% 3-HB(F)VB-2 4.0% 3-HB(F)VB-3 4.0%

Characteristics of the composition were determined as follows:

TNI=90.2(° C.)

η=24.1(mPa.s)

Δn=0.128

Δε=5.0

Vth=2.29(V)

COMPOSITION EXAMPLE 17

101-HHB(F,F)-OCF3 (No. 153) 10.0%  5-H10BB(F,F)-OCF3 (No. 239) 5.0% 3-HHB(F,F)-F 9.0% 3-H2HB(F,F)-F 8.0% 4-H2HB(F,F)-F 8.0% 3-HBB(F,F)-F 21.0%  5-HBB(F,F)-F 13.0%  3-H2BB(F,F)-F 10.0%  5-HHBB(F,F)-F 3.0% 5-HHEBB-F 2.0% 3-HH2BB(F,F)-F 3.0% 101-HBBH-4 4.0% 101-HBBH-5 4.0%

Characteristics of the composition were determined as follows:

TNI=98.1(° C.)

η=40.4(mPa.s)

Δn=0.116

Δε=9.9

Vth=1.62(V)

COMPOSITION EXAMPLE 18

101-HHB(F,F)-OCF3 (No. 153) 5.0% 5-H10BB(F,F)-OCF3 (No. 239) 5.0% 5-HB-F 12.0%  6-HB-F 9.0% 7-HB-F 7.0% 2-HHB-OCF3 7.0% 3-HHB-OCF3 7.0% 4-HHB-OCF3 7.0% 3-HH2B-OCF3 4.0% 5-HH2B-OCF3 4.0% 3-HHB(F,F)-OCF3 5.0% 3-HBB(F)-F 10.0%  5-HBB(F)-F 5.0% 3-HH2B(F)-F 3.0% 3-HB(F)BH-3 3.0% 5-HBBH-3 3.0% 3-HHB(F,F)-OCF2H 4.0%

Characteristics of the composition were determined as follows:

COMPOSITION EXAMPLE 19

101-HHB(F,F)-OCF3 (No. 153) 5.0% 101-HB(F,F)B(F,F)-OCF3 (No. 187) 5.0% 2-HHB(F)-F 2.0% 3-HHB(F)-F 2.0% 5-HHB(F)-F 2.0% 2-HBB(F)-F 6.0% 3-HBB(F)-F 6.0% 5-HBB(F)-F 5.0% 2-H2BB(F)-F 9.0% 3-H2BB(F)-F 4.0% 3-HBB(F,F)-F 25.0%  5-HBB(F,F)-F 19.0%  101-HBBH-4 5.0% 101-HBBH-5 5.0%

COMPOSITION EXAMPLE 20

101-HHB(F,F)-OCF3 (No. 153) 8.0% 5-H10BB(F,F)-OCF3 (No. 239) 8.0% 7-HB(F)-F 5.0% 5-H2B(F)-F 5.0% 3-HB-02 10.0%  3-HH-4 2.0% 3-HB[5D,6D,7D]-4 3.0% 3-HHB(F)-F 10.0%  5-HH[5D,6D,7D]B(F)-F 10.0%  3-H2HB(F)-F 5.0% 2-HBB(F)-F 3.0% 3-HBB(F)-F 3.0% 5-HBB(F)-F 6.0% 2-H2BB(F)-F 5.0% 3-HHB-1 8.0% 3-HHB-01 5.0% 3-HHB-3 4.0%

Characteristics of the composition were determined as follows:

TNI=87.2(° C.)

η=26.3(mPa.s)

Δn=0.094

Δε=4.4

Vth=2.50(V)

COMPOSITION EXAMPLE 21

101-HHB(F,F)-OCF3 (No. 153) 10.0% 5-H10BB(F,F)-OCF3 10.0% 7-HB(F,F)-F  3.0% 3-H2HB(F,F)-F 12.0% 4-H2HB(F,F)-F 10.0% 3-HHB(F,F)-F  5.0% 4-HHB(F,F)-F  5.0% 3-HH2B(F,F)-F 15.0% 3-HBB(F,F)-F 12.0% 5-HBB(F,F)-F 12.0% 3-HBCF20B(F,F)-F  6.0%

Characteristics of the composition were determined as follows:

TNI=70.8(° C.)

η=35.8(mPa.s)

Δn=0.092

Δε=9.9

Vth=1.43(V)

COMPOSITION EXAMPLE 22

101-HHB(F,F)-OCF3 (No. 153) 10.0%  5-H10BB(F,F)-OCF3 (No. 239) 5.0% 7-HB(F,F)-F 5.0% 3-H2HB(F,F)-F 12.0%  4-H2HB(F,F)-F 10.0%  3-HHB(F,F)-F 10.0%  4-HHB(F,F)-F 5.0% 3-HBB(F,F)-F 10.0%  4-HHEB(F,F)-F 3.0% 5-HHEB(F,F)-F 3.0% 2-HBEB(F,F)-F 3.0% 3-HBEB(F,F)-F 5.0% 5-HBEB(F,F)-F 3.0% 3-HGB(F,F)-F 10.0%  3-HHBB(F,F)-F 6.0%

Characteristics of the composition were determined as follows:

TNI=74.8(° C.)

η=39.5(mPa.s)

Δn=0.088

Δε=13.8

Vth=1.32(V)

COMPOSITION EXAMPLE 23

101-HHB(F,F)-OCF3 (No. 153) 5.0% 5-H10BB(F,F)-OCF3 (No. 239) 5.0% 5-H4HB(F,F)-F 7.0% 5-H4HB-OCF3 15.0%  3-H4HB(F,F)-CF3 8.0% 5-H4HB(F,F)-CF3 5.0% 3-HB-CL 6.0% 5-HB-CL 4.0% 2-H2BB(F)-F 5.0% 3-H2BB(F)-F 5.0% 5-HVHB(F,F)-F 5.0% 3-HHB-OCF3 5.0% 3-H2HB-OCF3 5.0% V-HHB(F)-F 5.0% 3-HHB(F)-F 5.0% 5-HHEB-OCF3 2.0% 3-HBEB(F,F)-F 5.0% 5-HH-V2F 3.0%

Characteristics of the composition were determined as follows:

TNI=69.3(° C.)

η=28.9(mPa.s)

Δn=0.093

Δε=8.8

Vth=1.67(V)

COMPOSITION EXAMPLE 24

5-H10BB(F,F)-OCF3 (No. 239) 5.0% 101-HHB(F,F)-OCF3 (No. 153) 5.0% 5-H01BB(F,F)-OCF3 (No. 241) 5.0% 3-HH10BB(F,F)-OCF3 (No. 692) 3.0% 5-BEB(F)-C 5.0% V-HB-C 11.0%  5-PyB-C 6.0% 4-BB-3 6.0% 3-HH-2V 2.0% 5-HH-V 11.0%  V-HHB-1 7.0% V2-HHB-1 10.0%  3-HHB-1 9.0% 1V2-HBB-2 10.0% 3-HHEBH-3 5.0%

COMPOSITION EXAMPLE 25

3-B10B(F,F)-OCF3 (No. 122) 3.0% 3-H10B(F,F)-OCF3 (No. 118) 3.0% 3-HH10B(F,F)-OCF3 (No. 235) 5.0% 101-HVHB(F,F)-OCF3 (No. 165) 5.0% 1V2-BEB(F,F)-C 8.0% 3-HB-C 10.0%  V2V-HB-C 14.0%  V2V-HH-3 13.0%  3-HB-02 4.0% 3-HHB-1 10.0%  3-HHB-3 9.0% 3-HB(F)TB-2 4.0% 3-HB(F)TB-3 4.0% 3-H2BTB-3 4.0% 3-H2BTB-4 4.0%

COMPOSITION EXAMPLE 26

101-HGB(F,F)-OCF3 (No. 212) 3.0% 301-HB(F)B(F,F)-OCF3 (No. 202) 3.0% 101-H2HB(F,F)-OCF3 (No. 160) 3.0% 101-H2B(F,F)B(F,F)-OCF3 (No. 192) 3.0% 1V2-BEB(F,F)-C 4.0% 3-HB-C 18.0%  2-BTB-1 10.0%  5-HH-VFF 30.0%  1-BHH-VFF 6.0% 1-BHH-2VFF 11.0%  3-H2BTB-2 5.0% 3-HHB-1 4.0%

COMPOSITION EXAMPLE 27

101-HHB(F,F)-OCF3 (No. 153) 4.0% 5-H10BB(F,F)-OCF3 (No. 239) 4.0% 101-HGB(F,F)-OCF3 (No. 212) 4.0% 5-H01BB(F,F)-OCF3 (No. 241) 4.0% 3-HH10B(F,F)-OCF3 (No. 235) 4.0% 101-HVHB(F,F)-OCF3 (No. 165) 4.0% 3-H2HB(F,F)-F 7.0% 3-HHB(F,F)-F 10.0%  4-HHB(F,F)-F 5.0% 3-HH2B(F,F)-F 9.0% 3-HBB(F,F)-F 15.0%  5-HBB(F,F)-F 15.0%  3-HBEB(F,F)-F 2.0% 4-HBEB(F,F)-F 2.0% 5-HBEB(F,F)-F 2.0% 3-HHEB(F,F)-F 3.0% 4-HHEB(F,F)-F 3.0% 5-HHEB(F,F)-F 3.0%

COMPOSITION EXAMPLE 28

101-HB(F,F)-OCF3 (No. 1) 4.0% 3-B10B(F,F)-OCF3 (No. 122) 4.0% 3-HH10BB(F,F)-OCF3 (No. 692) 4.0% 301-HB(F)B(F,F)-OCF3 (No. 200) 4.0% 101-H2B(F,F)B(F,F)-OCF3 (No. 192) 4.0% 5-HB-CL 12.0%  3-HH-4 7.0% 3-HB-02 15.0%  3-H2HB(F,F)-F 8.0% 3-HHB(F,F)-F 3.0% 3-HBB(F,F)-F 6.0% 3-HHB(F)-F 5.0% 2-H2HB(F)-F 2.0% 3-H2HB(F)-F 1.0% 5-H2HB(F)-F 2.0% 3-HHBB(F,F)-F 4.0% 3-HBCF20B-OCF3 4.0% 5-HBCF20B(F,F)-CF3 4.0% 3-HHB-1 3.0% 3-HHB-01 4.0%

COMPOSITION EXAMPLE 29

101-HHB(F,F)-OCF3 (No. 153) 5.0% 3-HH10B(F,F)-OCF3 (No. 235) 5.0% 301-HB(F)B(F,F)-OCF3 (No. 200) 10.0%  101-H2HB(F,F)-OCF3 (No. 160) 10.0%  101-H2B(F,F)B(F,F)-OCF3 (No. 192) 10.0%  2-HHB(F)-F 17.0%  3-HHB(F)-F 17.0%  5-HHB(F)-F 12.0%  3-H2HB(F)-F 5.0% 3-HBB(F)-F 6.0% 5-HBB(F)-F 3.0%

COMPOSITION EXAMPLE 30

101-HHB(F,F)-OCF3 (No. 153) 5.0% 5-H10BB(F,F)-OCF3 (No. 239) 5.0% 5-H01BB(F,F)-OCF3 (No. 241) 5.0% 3-HH10B(F,F)-OCF3 (No. 235) 5.0% 3-HH10BB(F,F)-OCF3 (No. 692) 5.0% 301-HB(F)B(F,F)-OCF3 (No. 200) 10.0%  101-H2HB(F,F)-OCF3 (No. 160) 5.0% 101-H2B(F,F)B(F,F)-OCF3 (No. 192) 10.0%  7-HB(F,F)-F 5.0% 3-HHB(F,F)-F 10.0%  3-HBB(F,F)-F 10.0%  3-HHEB(F,F)-F 8.0% 4-HHEB(F,F)-F 3.0% 5-HHEB(F,F)-F 3.0% 2-HBEB(F,F)-F 3.0% 3-HBEB(F,F)-F 5.0% 5-HBEB(F,F)-F 3.0%

Compounds of the present invention expressed by the general formula (1) can be produced by known methods of ordinary organic synthesis as illustrated below.

(A) Production of compounds expressed by the general formula (1) in which B₃ a single bond and A₃ is 1,4-cyclohexylene group:

An alcohol expressed by (24-1) or (25-1) can easily be synthesized by reacting ketone (19) with compounds (22) or (23) which are prepared from 4-bromo-2, 6-difluorotrifluoromethoxybenzene (20) or 4-bromo-2, 6-difluorobenzene (21) according to the method described in Jikken Kagaku Koza, Vol.20, p96, Maruzen. Herein, the compound (19) can easily be synthesized according to the similar methods described in Organic Functional Group Preparations, Vol.1, p206, Academic Press or The Fourth Edition of Jikken Kagaku Koza, Vol.21, p149, Maruzen.

Then, cyclohexene derivative expressed by (24-2) or (25-2) can easily be synthesized by dehydrating thus obtained alcohol in the presence of an acid catalyst such as toluene sulfonic acid according to the conventional method.

The derivative compound can then be reduced in the presence of such a catalyst as Raney nickel according to the conventional method, to synthesize easily a compound which has trifluoromethyl group as Rf in the general formula (1) or a compound shown by (25-3).

wherein R, A₁, A₂, B₁, B₂, k, m and n have the same meanings as above.

The compound (25-3) is further converted into a compound expressed by the general formula (1) by carrying out the following reactions. That is, the compound (25-3) is reacted with n-BuLi, followed by reaction with triisopropyl borate, and then treated with an acid according to the method described in The Chemistry of Boron, Academic Press, New York, (1961), which shares similar method described as above to be converted into compound (25-4). The said compound is reacted with hydrogen peroxide according to the method described in Tetrahedron Lett., 21, 3435 (1980) or so to be converted into a phenol derivative expressed by (25-5), and this derivative is easily converted into a compound expressed by the general formula (1) according to known methods.

That is, compounds expressed by the general formula (1) wherein Rf is CF₂H, C₂F₅, CHFCF₃, CF₂CF₂H, CH₂CF₃, CHFCF₂H, CH₂CF₂H, CF₂CH₃, CF₂CFHCF₃, CH₂CF₂CF₂H, CF₂CH₂CF₃, CF₂CH₂CH₃ or CH₂CH₂CF₃ can easily be synthesized according to the known methods described in DE 4027840 A1, WO 9426338 A1, DE 4445224 A1, DE 19528085 A1, DE 4142519 A1, DE 4222371 A1, DE 19531165 A1, WO 9221734 A1, WO 9212928 A1, WO Laid-open Japanese Patent Publication No. Hei 8-510220, Laid-open Japanese Patent Publication No. Hei 7-18184 or Laid-open Japanese Patent Publication No. Hei 6-40988.

wherein R, A₁, A₂, B₁, B₂, k, m, n and Rf have the same meanings as above.

Further, compounds in which Rf is CF₂CF₂CH₃ or CFHCF₂CF₃ can easily be synthesized by the following methods. That is, in the case of CF₂CF₂CH₃, the compound (25-5) is converted into a compound (25-6) according to the method described in J. Chem. Soc. Perkin Trans. 1, 439 (1994) etc., and then the compound (25-6) is converted into the objective compound by fluorination of carbonyl oxygen thereof with SF₄/HF or so according to the similar method described in WO 9426838 A1 etc.

In the case of CFHCF₂CF₃, the compound (25-5) is converted into a compound (25-7) according to the similar method described in DE 4445224 A1 etc., and then the compound (25-7) is converted into the objective compound by fluorination of hydroxide group thereof with diethyl aminosulfate trifluoride (DAST) or so.

wherein R, A₁, A₂, B₁, B₂, k, m and n have the same meanings as above.

(B) Production of compounds expressed by the general formula (1) in which B₃is a single bond and A₃ is 1,4-phenylene or pyrimidine-2, 5-diyl group in each of which any hydrogen atom on the rings may optionally be substituted with a fluorine atom:

A compound (1) or (29) can easily be synthesized by reacting a halide (26) with a boric acid derivative (27) or (28) in the presence of a palladium catalyst or so according to the method described in Comprehensive Organometallic Chemistry, Vol.12, p 192, Pergamon etc.

Herein, the compound (26) can easily be synthesized according to the similar method described in Organic Functional Group Preparations, Vol.1, p148, Academic Press and Shin Jikken Kagaku Koza, Vol.14, p307, Maruzen etc., and the compound (27) or (28) can easily be synthesized according to the similar method described in The Fourth Edition of Jikken Kagaku Koza 24, Organic Synthesis VI, p80, Maruzen.

wherein R, A₁, A₂, A₃, B₁, B₂, k, m and n have the same meanings as above, and Y denotes halogen or trifluoromethanesulfonate group.

Furthermore, the compound (29) is easily converted into the compound expressed by the general formula (1) by carrying out the similar reactions to the above-mentioned (25-3).

The said compound can easily be synthesized by the following method. That is, the compound (1) or (29) can easily be synthesized by reacting a zinc complex (30) with compound (20) or (21) in the presence of a palladium catalyst or a platinum catalyst or so.

wherein R, A₁, A₂, A₃, B₁, B₂, k, m, and n have the same meanings as above.

(C) Production of compounds expressed by the general formula (1) in which B₃ is a single bond and A₃ is dioxane-2, 5-diyl group:

A compound (1) or (34) can easily be synthesized by dehydrating and condensing diol (31) with aldehyde (32) or (33) in the presence of an acid catalyst such as toluenesulfonic acid according to the method described in J. Chem. Soc., Perkin Trans. I, 158, (1979) etc. Herein, the compound (31) can easily be synthesized according to the similar method described in Org. Chem., 32, 113 (1967) etc., and the compound (32) can easily be synthesized from (20) according to the similar method described in Comprehensive Organic Functional Group Transformations, Vol.3, p1, Pergamon etc.

wherein R, A₁, A₂, B₁, B₂, k, m and n have the same meanings as above.

The compound (34) can easily be converted into the compound expressed by the general formula (1) by carrying out the similar reactions to the above-mentioned (25-3).

(D) Production of compounds expressed by the general formula (1) in which B₃ is 1,2-ethylene, (E)-1,2-ethenylene or 1,4-butylene group:

A compound expressed by the general formulae (1), (36-2) or (37-2) can easily be synthesized by the similar method to (A) above-mentioned. Herein, the compound (35) can easily be synthesized according to the similar method described in Comprehensive Organic Functional Group Transformations, Vol.3, p 1, Pergamon and Shin Jikken Kagaku Koza, Vol. 14, p633, Maruzen etc.

wherein R, A₁, A₂, A₃, B₁, B₂, k, m and n have the same meanings as above.

The compound (37-2) can easily be converted into the compound expressed by the general formula (1) in which B₃ is (E)-1,2-ethenylene group by carrying out the similar reactions to the above-mentioned (25-3).

The compound (36-2) or (37-2) is easily converted into the compound expressed by the general formula (1) or (37-3) in which B₃ is 1,2-ethylene or 1,4-butylene group by hydrogenation.

wherein R, A₁, A₂, A₃, B₁, B₂, k, m and n have the same meanings as above and r denotes 1 or 3.

The compound (37-3) can easily be converted into the compound expressed by the general formula (1) in which B₃ is 1,2-ethylene or 1,4-butylene group by carrying out the similar reactions to the above-mentioned.

(E) Production of compounds expressed by the general formula (1) in which B₃ is 1,2-ethynylene group:

By converting the above-mentioned compound (36-2) or (37-2) into (36-4) or (37-4) according to the method described in J. Am. Chem. Soc., 89, 6149 (1967) etc. and then treating them with a base, the compound (1) or (37-5) in which B₃ is 1,2-ethynylene group can easily be obtained.

wherein R, A₁, A₂, A₃, B₁, B₂, k, m and n have the same meanings as above.

The compound (37-5) can easily be converted into the compound expressed by the general formula (1) by carrying out the similar reactions to the above.

(F) Production of compounds expressed by the general formula (1) in which B₃ is oxymethylene group:

A compound (1) or (41) can easily be synthesized by reacting alcohol (38) with halide (39) or (40) according to the method described in Comprehensive Organic Functional Group Transformations, Vol. 2, p88, Pergamon etc. Herein, the compound (38) can easily be synthesized according to the similar method described in Comprehensive Organic Functional Group Transformations, Vol.2, p37, Pergamon etc., and the compound (39) or (40) can easily be synthesized from the compound (20) or (21) above-mentioned and according to the similar method described in J. Am. Chem. Soc., 89, 6149 (1967) and Shin Jikken Kagaku Koza, Vol.14, p307, Maruzen etc.

wherein R, A₁, A₂, A₃, B₁, B₂, k, m, n and Y have the same meanings as above.

The compound (41) can easily be converted into the compound expressed by the general formula (1) by carrying out the similar reactions as above.

(G) Production of compounds expressed by the general formula (1) in which B₃ is methyleneoxy group:

A compound (1) or (45) can easily be synthesized according to the similar method as above-mentioned (F). Herein, the compound (43) can easily be synthesized according to the similar method described in J. Am. Chem. Soc., 79, 5659 (1957).

wherein R, A₁, A₂, A₃, B₁, B₂, k, m, n and Y have the same meanings as above.

The compound (45) can easily be converted into the compound expressed by the general formula (1) by carrying out the similar reactions as above-mentioned (25-3).

(H) Production of compounds expressed by the general formula (1) in which B₃ is carbonyloxy group:

The compound expressed by the general formula (1) in which Rf is trifluoromethyl group can easily be synthesized by condensing carboxylic acid (46) and the compound (43) above-mentioned in the presence of dicyclohexylcarbdiimide or so according to the method described in Jikken Kagaku Koza, Vol.22, p43, Maruzen. Herein, the compound (46) can easily be synthesized according to the similar method described in Organic Functional Group Preparations, Vol.1, p236, Academic Press etc.

wherein R, A₁, A₂, A₃, B₁, B₂, k, m and n have the same meanings as above.

The compounds in which Rf is other than trifluoromethyl group can be synthesized by the following method.

That is, the compound (47) derived from 3,5-difluorophenol is let to a similar reaction as that of (25-3) above-mentioned to synthesize a compound (48), and then the benzyl group of the compound (48) is deprotected by hydrogenation to synthesize easily the phenol expressed by (49).

wherein Rf has the same meaning as above.

Also, those in which ring A is a silacyclohexane ring can be synthesized by using the starting compounds of the general formulae (19), (26), (30), (31), (35), (38), (42) and (46) prepared according to the method described in Laid-open Japanese Patent Publication No.Hei 7-70148 and Laid-open Japanese Patent Publication No.Hei 8-239388 etc.

After the reaction, the above-mentioned compound (1) is let to a conventional after-treatment and then to operations such as distillation, recrystallization, column chromatography or so, to be purified and isolated.

EXAMPLE

The following examples illustrate the present invention in more detail without limiting it to those examples. In every examples, C denotes crystals, N denotes a nematic phase, S denotes a smectic phase, I denotes isotropic liquid, and the phase transition temperatures are all given by unit of ° C.

Example 1

Synthesis of 2,6-difluoro-4-(trans-4-(trans-4-methoxymethyl cyclohexyl) cyclohexyl) trifluoromethoxybenzene (compound expressed by the general formula (1) wherein R is methyl group, k=1, m=0, n=1, A₂ and A₃ are both 1,4-cyclohexylene groups, B₂ and B₃ are both single bonds, and Rf is triiluoromethyl group (Compound No. 153))

1.2 g (49 mmol) of magnesium was added in tetralydrofuran (hereinafter abbreviated to THF, 50 ml), and 13 g (47 mmol) of 4-bromo-2,6-difluorotrifluoromethoxybenzene dissolved in THF (80 ml) was dropwise added thereto, followed by stirring at a room temperature for 1.5 hours. To the reaction solution was dropwise added 10 g (45mmol) of 4-(4-methoxymethylcyclohexyl) cyclohexanone dissolved in THF (80 ml) and reaction was carried out at a room temperature for one night. This reaction solution was added with a saturated aqueous ammonium chloride solution (180 ml) and then extracted twice with toluene (100 ml). The organic layer thus obtained was washed with brine (200 ml), dried over anhydrous magnesium sulphate and filtered, and the solvent therein was distilled off under a reduced pressure. The compound thus obtained was used for subsequent reaction without any purification. 18 g (yield 96%).

18 g (43 mmol) of the alcohol derivative obtained above and 3.0 g (22 mmol) of potassium hydrogen sulfate were refluxed in toluene for 3 hours with removing produced water. After cooling, the reaction solution was filtered and the solvent therein was distilled off under a reduced pressure.

The residue thus obtained was purified by column chromatography (silica gel/toluene) and recrystallization (heptane) to obtain colorless crystals of 2,6-difluoro-4-(4-(trans-4-methoxymethylcyclohexyl)-1-cyclohexenyl) trifluoromethoxybenzene.

6.9 g (yield 40%).

6.8 g (17 mmol) of this compound was dissolved in a mixed solvent of toluene-alcohol (1/1 v/v, 200 ml) and hydrogenated in the presence of a Raney nickel catalyst for one night (under hydrogen pressure of 800 kPa). The reaction mixture was filtered and the solvent therein was distilled off under a reduced pressure. The residue thus obtained was purified by column chromatography (silica gel/toluene) and recrystallization heptane) to obtain objective colorless crystals of 2,6-difluoro-4-(trans-4-(trans-4-methoxymethylcyclohexyl) cyclohexyl)trifluoromethoxy benzene.

4.2 g (yield 61%).

Various spectral data of this compound and intermediate compounds in respective step well support the constitutions thereof.

Phase transition temperature C·76.0·N99.9·I

MS m/e =406 (M+). 1H NMR: δ (ppm) 6.84 (dd, 2H, J=11.0, 2.0 Hz), 3.33 (s, 3H), 3.18 (d, 2H, J=6.1 Hz), 2.7-0.5 (m, 20H).

19F NMR; δ (ppm) −60.3 (3F) −126.1 (2F).

Example 2

Synthesis of 2,6-difluoro-4-(4-(trans-4-methoxymethylcyclohexyl)-2,6-difluorophenyl) trifluoromethoxy benzene (compound expressed by the general formula (1) wherein R is methyl group, k=1, m=0, n=1, A₂ is 1,4-cyclohexylene group, A₃ is 3,5-difluoro-1, 4-phenylene group, B₂ and B₃ are single bonds, and Rf is trifluoromethyl group (Compound No. 187))

9.2 g (39 mmol) of 3,5-difluoro-1-(4-methoxymethyl) cyclohexyl benzene was dissolved in THF (80 ml). This solution was added with 28 ml of n-BuLi containing hexane solution (1.65M) (46.2 mmol) at a temperature of −60° C. or lower and was stirred for 20 minutes. To the reaction mixture, 93 ml of zinc chloride containing THF solution (0.5M) (96.5 mmol) was added at a temperature of −45° C. or lower and the solution was stirred until the time when the mixture was warmed up to a room temperature.

To the reaction mixture, 13 g (47 mmol) of 4-bromo-2, 6-difluorotrifluoromethoxybenzene and 1.0 g (0.86 mmol) of tetrakistriphenylphosphine palladium (0) both dissolved in THF (50 ml) were added and the reaction mixture was refluxed for 5 hours. After cooling, 3N HCl (100 ml) was added thereto to separate an organic layer, while an aqueous layer was further extracted with toluene (200 ml). The organic layer was washed with a saturated sodium hydrogen carbonate solution (150 ml), then dried over anhydrous magnesium sulfate and filtered, and the solvent therein was distilled off under a reduced pressure.

The residue thus obtained was purified by column chromatography (silica gel/toluene: ethyl acetate=20:1) and to obtain colorless crystals of 2,6-difluoro-4-(4-(trans-4-methoxymethylcyclohexyl)-2,6-difluorophenyl) trifluoromethoxybenzene.

2.1 g (yield 12%).

Various spectral data of this compound and intermediate compounds in respective step well support the constitutions thereof.

Phase transition temperature C·75.4·I MS m/e=436 (M+). 1H NMR: δ (ppm) 6.8-7.0, 7.0-7.3 (m, 4H), 3.36 (s, 3H), 3.25(d, 2H, 5.7 Hz), 2.8-0.8 (m, 10H). 19F NMR; δ (ppm) −60.1 (3F), −115.3 (2F), −125.6 (2F).

Example 3

Synthesis of 2,6-difluoro-4-(4-(trans-4-pentylcyclohexyl) methoxyphenyl) trifluoromethoxybenzene (compound expressed by the general formula (1) wherein R is pentyl group, k=0, m=0, n=1, A₂ is 1,4-cyclohexylene group, A₃ is 1,4-phenylene group, B₃ is methyleneoxy group, B₃ is a single bond, and Rf is trifluoromethyl group (Compound No. 239)

A mixture of 5.0 g (13 mmol) of 4-(trans-4-pentylcyclohexyl) methoxyiodo benzene, 4.1 g (34 mmol) of dihydroxy (3,5-difluoro-4-trifluoromethoxyphenyl) borane, 3.0 g of 5% palladium on activated charcoal and 7.2 g (136 mmol) of sodium carbonate was refluxed in toluene/alcohol/water (1/1/1 v/v, 75 ml) under a nitrogen atmosphere for 3 days. After cooling, the reaction solution was added with water (100 ml) and extracted twice with toluene (100 ml). An organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent therein was distilled off under a reduced pressure. The residue thus obtained was purified by column chromatography (silica gel/heptane:toluene=5:1) and recrystallization (heptane-ethanol) to obtain colorless crystals of 2,6-difluoro-4-(4-(trans-4-pentylcyclohexyl) methoxyphenyl) trifluoromethoxybenzene.

3.7 g (yield 62%).

Various spectral data of this compound and intermediate compounds in respective step well support the constitutions thereof.

Phase transition points C·67.4·N·83.9·I MS m/e=456 (M+). 1H NMR: δ (ppm) 7.6-7.4, 7.3-6.8 (m, 6H), 3.79 (d, 2H, J=5.7 Hz), 2.2-0.6 (m, 21H). 19F NMR; δ (ppm) −60.3 (3F), −125.2 (2F).

Example 4

Synthesis of 2,6-difluoro-4-(trans-4-(trans-4-methoxymethyl cyclohexyl) cyclohexyl) difluoromethoxybenzene (compound expressed by the general formula (1) wherein R is methyl group, k=1, m=0, n=1, A₂ and A₃ are both 1,4-cyclohexylene groups, B₂ and B₃ are both single bonds, and Rf is difluoromethyl group (Compound No. 269))

1.5 g (62 mmol) of magnesium was added to THF (50 ml), and the resultant solution was dropwise added with 11 g (57 mmol) of 3,5-difluorobromobenzene dissolved in THF (50 ml) and was stirred at a room temperature for one hour.

The reaction solution was dropwise added with 12 g (55 mmol) of 4-(4-methoxymethyl cyclohexyl) cyclohexanone dissolved in THF (100 ml), reacted at a room temperature overnight and then let to a similar after-treatments as described in Example 1 to obtain the objective compound. This compound was used for the subsequent reaction without any purification. 18 g (yield 97%).

18 g (54 mmol) of the alcohol derivative obtained above and 2.0 g (11 mmol) of p-toluenesulfonic acid were refluxed in toluene for 2 hours with removing produced water. After cooling, the reaction solution was filtered and the solvent therein was distilled off under a reduced pressure. The residue thus obtained was purified by column chromatography (silica gel/toluene) to obtain colorless crystals of 3,5-difluoro-1-(4-(trans-4-methoxymethylcyclohexyl)-1-cyclohexenyl) benzene.

12 g (yield 67%).

12 g (36 mmol) of this compound was dissolved in a mixed solvent of toluene-alcohol (1/1 v/v, 200 ml) and hydrogenated in the presence of a Raney nickel catalyst for two days (under hydrogen pressure of 800 kPa). The reaction mixture was filtered and the solvent therein was distilled off under a reduced pressure. The residue thus obtained was purified by recrystallization (heptane-ethanol) to obtain colorless crystals of 3,5-difluoro-1-(trans-4-(trans-4-methoxymethylcyclohexyl) cyclohexyl) benzene.

6.3 g (yield 54%).

5.0 g (16 mmol) of this compound was dissolved in THF (50 ml). This solution was added with 11 ml of n-BuLi containing hexane solution (1.65M) (19 mmol) at a temperature of −60° C. or lower and was stirred at the same temperature for 20 minutes. To the reaction mixture, 4.3 ml (19 mmol) of triisopropyl borate dissolved in THF (30 ml) was dropwise added at a temperature of −50° C. or lower. After the addition, a dry ice bath was removed and the mixture was let to stand until time when it was cooled down to a room temperature. The reaction mixture was added with water (40 ml) at a temperature of −30° C. or lower and stirred at a room temperature for 1 hour, and added further with aqueous 3N HCl solution (40 ml) and reacted at a room temperature for 2 hours. After separation of an organic layer, an aqueous layer was further extracted with ether (100 ml). The organic layer was washed with saturated brine (100 ml), dried over anhydrous magnesium sulfate and filtered, and the solvent therein was distilled off under a reduced pressure. This obtained compound was-used for subsequent reaction without any purification.

5.1 g (yield 90%).

5.1 g (14 mmol) of this boronic acid derivative was dissolved in THF (50 ml) and 36% aqueous hydrogen peroxide solution (3.2 ml) was added thereto at 0° C., followed by stirring for 36 hours. The reaction mixture was added with a saturated aqueous sodium thiosulfate solution (40 ml) and reacted at a room temperature for 15 minutes, added with 3N HCl aqueous solution (40 ml) and then extracted with ethyl acetate (50 ml) three times. The organic layer was washed with saturated brine (50 ml), dried over anhydrous magnesium sulfate and filtered, and the solvent therein was distilled off under a reduced pressure.

The residue thus obtained was recrystallized with toluene to obtain colorless crystals of 2,6-difluoro-4-(trans-4-(trans-4-methoxymethylcyclohexyl) cyclohexyl) phenol.

3.1 g (yield 66%).

3.0 g (8.9 mmol) of this compound, 2.2 g (55 mmol) of NaOH and 110 mg (0.63 mmol) of Na₂S₂O₄ were dissolved in a mixed solvent of dioxaneisopropanol-water (1/1/1 v/v/v 30 ml), and the solution was stirred at 60° C. for 9 hours after the vessel containing the contents was purged with CHF₂Cl gas.

2.2 g (55 mmol) of NaOH and 110 mg (0.63 mmol) of Na₂S₂O₄ were added to the reaction mixture, and the mixture was further stirred at 60° C. for overnight after the vessel was purged with CHF₂Cl gas. After cooled, the reaction mixture was added with 3N HCl aqueous solution (150 ml) and extracted with toluene (150 ml). The organic layer was washed with an aqueous sodium hydrogen carbonate solution (150 ml), dried over anhydrous magnesium sulfate and filtered. The solvent therein was distilled off under a reduced pressure and the residue thus obtained was purified by column chromatography (silica gel/toluene) and recrystallization (heptane-ethanol) to obtain colorless crystals of 2,6-difluoro-4-(trans-4-(trans-4-methoxymethylcyclohexyl) cyclohexyl) difluoromethoxybenzene.

1.8 g (yield 53%).

Various spectral data of this compound and intermediate compounds in respective step well support the constitutions thereof.

Phase transition temperature C·57.9·N·101.7·I MS m/e=388 (M+). 1H NMR: δ (ppm) 7.0-6.7 (m, 4H), 6.53 (t, 1H, J=74.1 Hz), 3.33 (s, 3H), 3.18 (d, 2H, J=5.9 Hz), 2.7-0.5 (m, 20H). 19F NMR; δ (ppm) −82.8 (2F), −126.9 (2F).

Example 5

Synthesis of 4-(2-(4-(4-ethoxymethylcyclohexyl) cyclohexyl) ethyl) phenyl)-2,6-difluorotrifluoromethoxybenzene (compound expressed by the general formula (1) wherein R is ethyl group, k=1, m=n=1, A₁ and A₂ are 1, 4-cyclohexylene groups, A₃ is 1,4-phenylene group, B₁ and B₃ are single bonds, B₂ is 1,2-ethylene group and Rf is trifluoromethyl group (Compound No. 615)

6.3 g (13 mmol) of 4-(2-(4-(4-ethoxymethylcyclohexyl) cyclohexyl) ethyl) trifluoromethylsulfonyloxybenzene, 4.2 g (17 mmol) of dihydroxy (3,5-difluoro-4-trifluoromethoxyphenyl) borane, 5% palladium on activated charcoal (1.0 g) and 5.7 g (54 mmol) of sodium carbonate were refluxed in toluene/alcohol/water (1/1/1 v/v, 80 ml) under a nitrogen atmosphere for 3 days. After cooling, the reaction solution was added with water (150 ml) and extracted twice with toluene (150 ml). An organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent therein was distilled off under a reduced pressure. The residue thus obtained was purified by column chromatography (silica gel/heptane:toluene=5:1) and recrystallization (heptane-ethanol) to obtain colorless crystals of 4-(4-(2-(4-(4-ethoxymethylcyclohexyl)cyclohexyl)ethyl)phenyl)-2,6-difluorotrifluoromethoxybenzene.

2.4 g (yield 35%).

Various spectral data of this compound and compounds in respective step well support the constitutions thereof.

The following compounds 1 to 1252 can be prepared in accordance with the methods of Examples 1 to 5 above-mentioned.

k = 1, m = n = 0, R₁ = CF₃ No. R A₃ B₃ 1 CH3

— 2 n-C₃H₇

— 3 n-C₅H₁₁

— 4 CH₃

— 5 CH₃

6 n-C₃H₇

8 CH₃

— 9 n-C₃H₇

— 10 CH₃

11 n-C₃H₇

12 CH₃

13 CH₃

14 CH₃

— 15 n-C₃H₇

— 16 CH₃

17 n-C₃H₇

19 n-C₃H₇

20 CH₃

— 21 n-C₃H₇

23 CH₃

24 CH₃

— 25 CH₃

26 CH₃

— 27 n-C₃H₇

— 28 CH₃

29 CH3

— 30 n-C₃H₇

— 31 n-C₅H₁₁

— 32 CH₃

— 33 CH₃

34 n-C₃H₇

36 CH₃

— 37 n-C₃H₇

— 38 CH₃

39 n-C₃H₇

40 CH₃

41 CH₃

42 CH₃

— 43 n-C₃H₇

— 44 CH₃

45 n-C₃H₇

47 n-C₃H₇

48 CH₃

— 49 n-C₃H₇

51 CH₃

52 CH₃

— 53 CH₃

54 CH₃

— 55 n-C₃H₇

— 56 CH₃

k = 1, m = n = 0, R_(f) = CH₂CF₃ 57 CH3

— 58 n-C₃H₇

— 59 n-C₅H₁₁

— 60 CH₃

— 61 CH₃

62 n-C₃H₇

63 CH₃

—CO₂— 64 CH₃

— 65 n-C₃H₇

— 66 CH₃

67 n-C₃H₇

68 CH₃

69 CH₃

70 CH₃

— 71 n-C₃H₇

— 72 CH₃

73 n-C₃H₇

74 CH₃

—CO₂— 75 n-C₃H₇

76 CH₃

— 77 CH₃

— 78 n-C₃H₇

79 CH₃

80 CH₃

— 81 CH₃

82 CH₃

— 83 n-C₃H₇

— 84 CH₃

k = 1, m = n = 0, R_(f) = CF₂CFHCF₃ 85 CH3

— 86 n-C₃H₇

— 87 n-C₅H₁₁

— 88 CH₃

— 89 CH₃

90 n-C₃H₇

91 CH₃

—CO₂— 92 CH₃

— 93 n-C₃H₇

— 94 CH₃

95 n-C₃H₇

96 CH₃

97 CH₃

98 CH₃

— 99 n-C₃H₇

— 100 CH₃

101 n-C₃H₇

102 CH₃

—CO₂— 103 n-C₃H₇

104 CH₃

— 105 n-C₃H₇

106 CH₃

107 CH₃

108 CH₃

— 109 CH₃

110 CH₃

— 111 n-C₃H₇

— 112 CH₃

k = 0, m = = n = 0. R_(f) = CF₃ 113 CH₃

114 n-C₃H₇

115 n-C₅H₁₁

116 CH₃

117 CH₃

118 n-C₃H₇

119 CH₃

120 n-C₃H₇

121 CH₃

122 n-C₃H₇

123 CH₃

124 n-C₃H₇

125 CH₃

126 n-C₃H₇

127 CH₃

128 n-C₃H₇

129 CH₃

130 CH₃

131 CH₃

132 CH₃

k = 0, m = n = 0, R_(f) = CF₂H 133 CH₃

134 n-C₃H₇

135 n-C₅H₁₁

136 CH₃

137 CH₃

138 n-C₃H₇

139 CH₃

140 n-C₃H₇

141 CH₃

142 n-C₃H₇

143 CH₃

144 n-C₃H₇

145 CH₃

146 n-C₃H₇

147 CH₃

148 n-C₃H₇

149 CH₃

150 CH₃

151 CH₃

152 CH₃

K = 1, m = 0, n = 1, R₁ = CF₃ R A₂ B₂ A₃ B₃ 153 CH

—

— 154 C₂H₅

—

— 155 n-C₃H₇

—

— 156 n-C₅H₁₁

—

— 157 CH₃

—

158 C₂H₅

—

159 n-C₃H₇

—

160 CH₃

— 161 C₂H₅

— 162 n-C₃H₇

— 163 CH₃

—

164 CH₃

— 165 CH₃

— 166 n-C₃H₇

— 171 CH₃

—

— 172 C₂H₅

—

— 173 n-C₃H₇

—

— 174 n-C₅H₁₁

—

— 175 CH₃

—

176 n-C₃H₇

—

177 n-C₅H₁₁

—

178 CH₃

— — 179 C₂H₅

— — 180 n-C₃H₇

— 181 CH₃

—

182 n-C₃H₇

—

187 CH₃

—

— 188 C₂H₅

—

— 189 n-C₃H₇

—

— 190 CH₃

—

191 nC₃H₇

—

192 CH₃

— 193 n-C₃H₇

— R A₃ B₃ A₄ B₃ 194 CH₃

—

195 n-C₃H₇

—

199 CH₃

—

— 200 n-C₃H₇

— 201 CH₃

—

202 n-C₃H₇

—

203 CH₃

— 204 n-C₃H₇

— 205 n-C₃H₇

—

207 CH₃

—

— 208 n-C₃H₇

R A₂ B₂ A₃ B₃ 209 CH₃

—

212 CH₃

—

— 213 n-C₃H₇

—

— 214 CH₃

—

215 n-C₃H₇

—

216 CH₃

— 217 n-C₃H₇

— 220 CH₃

—

— 221 CH₃

—

222 CH₃

— 225 CH₃

—

— 226 n-C₃H₇

— 227 CH₃

—

228 CH₃

— 229 CH₃

—

— 230 CH₃

—

— 231 n-C₃H₇

—

— 232 CH₃

—

— 233 CH₃

—

— 234 CH₃

—

— 235 n-C₃H₇

—

236 n-C₅H₁₁

—

237

—

238 CH₃

— 239 n-C₅H₁₁

— 240 n-C₃H₇

— 241 n-C₅H₁₁

— 242 CH₃

—

243 n-C₃H₇

—

244 n-C₃H₇

— 245 n-C₅H₁₁

— 246 n-C₃H₇

— 247 n-C₅H₁₁

— 248 n-C₃H₇

—

249 n-C₃H₇

—

250 n-C₅H₁₁

— 251 n-C₃H₇

— 252 n--C₃H₇

—

253 n-C₅H₁₁

—

254 n-C₃H₇

— 255 nC₃H₇

— 256 n-C₃H₇

—

257 n-C₅H₁₁

— 258 n-C₃H₇

— 259 CH₃

—

260 n-C₃H₇

—

261 n-C₅H₁₁

— 262 CH₃

— 263 CH₃

—

264 n-C₃H₇

—

265 n-C₅H₁₁

— 266 n-C₃H₇

—

267 n-C₃H₇

—

268 n-C₅H₁₁

— k = 1, m = 0, n = 1, R_(f) = CF₂H 269 CH₃

—

— 270 C₂H₅

—

— 271 n-C₃H₇

—

— 272 n-C₅H₁₁

—

— 273 CH₃

—

274 C₂H₅

—

275 n-C₃H₇

—

276 CH₃

— 277 C₂H₅

— 278 n-C₃H₇

— 279 CH₃

—

280 CH₃

— 281 CH₃

— 282 n-C₃H₇

— 287 CH₃

—

— 288 C₂H₅

—

— 289 n-C₃H₇

—

— 290 n-C₅H₁₁

—

— 291 CH₃

—

292 n-C₃H₇

—

293 n-C₅H₁₁

—

294 CH₃

— 295 C₂H₅

— 296 n-C₃H₇

— 297 CH₃

—

298 n-C₃H₇

—

303 CH₃

—

— 304 C₂H₅

—

— 305 n-C₃H₇

—

— 306 CH₃

—

307 n-C₃H₇

—

308 CH₃

— 309 n-C₃H₇

— R A₃ B₃ A₄ B₃ 310 CH₃

—

311 n-C₃H₇

—

315 CH₃

—

— 316 n-C₃H₇

—

— 317 CH₃

—

318 n-C₃H₇

—

319 CH₃

— 320 n-C₃H₇

— 321 n-C₃H₇

—

323 CH₃

—

— 324 n-C₃H₇

—

— No. R A₂ B₂ A₃ B₃ 325 CH₃

—

326 CH₃

—

—CO₂— 327 CH₃

—CO₂—

— 328 CH₃

—

— 329 n-C₃H₇

—

— 330 CH₃

—

331 n-C₃H₇

—

332 CH₃

— 333 n-C₃H₇

— 336 CH₃

—

— 337 CH₃

—

338 CH₃

— 341 CH₃

—

— 342 n-C₃H₇

—

— 343 CH₃

—

344 CH₃

— 345 CH₃

—

— 346 CH₃

—

— 347 n-C₃H₇

—

— 348 CH₃

—

— 349 CH₃

—

— 350 CH₃

—

— 351 n-C₃H₇

—

352 n-C₅H₁₁

—

353

—

354 CH₃

— 355 n-C₅H₁₁

— 356 n-C₃H₇

— 357 n-C₅H₁₁

— 358 CH₃

—

359 n-C₃H₇

—

360 n-C₃H₇

— 361 n-C₅H₁₁

— 362 n-C₃H₇

— 363 n-C₅H₁₁

— 364 n-C₃H₇

—

365 n-C₃H₇

—

366 n-C₅H₁₁

367 n-C₃H₇

— 368 n-C₃H₇

—

369 n-C₅H₁₁

—

370 n-C₅H₇

— 371 n-C₃H₇

— 372 n-C₃H₇

—

373 n-C₅H₁₁

— 374 n-C₃H₇

— 375 CH₃

—

376 n-C₃H₇

—

377 n-C₅H₁₁

— 378 CH₃

— 379 CH₃

—

380 n-C₃H₇

—

381 n-C₅H₁₁

— 382 n-C₃H₇

—

383 n-C₃H₇

—

384 n-C₅H₁₁

— k = 0, m = 0, n = 1, R_(f) = CF₂H 385 CH₃

—

386 n-C₃H₇

— 387 CH₃

—

388 CH₃

— 389 CH₃

— 390 n-C₃H₇

—

—CO₂— 391 CH₃

—CO₂—

— 392 CH₃

—

393 CH₃

— 394 CH₃

—

395 CH₃

—

—CO₂— 396 CH₃

—CO₂—

— 397 CH₃

—

398 CH₃

— 399 CH₃

—

400 n-C₃H₇

—

—CO₂— 401 CH₃

—CO₂—

— 402 CH₃

—

R A₃ B₃ A₄ B₃ 403 CH₃

— 404 n-C₃H₇

—

405 CH₃

—

—CO₂— 406 CH₃

—

— 407 CH₃

—

408 CH₃

—

—CO₂— 409 CH₃

—CO₂—

— 410 CH₃

—

411 CH₃

— 412 CH₃

—

—CO₂— 413 n-C₃H₇

—CO₂—

— 414 CH₃

—

415 CH₃

— 416 CH₃

—

—CO₂— 417 n-C₃H₇

—CO₂—

— 418 CH₃

—

— 419 CH₃

—

420 CH₃

— 421 CH₃

—

— 422 CH₃

—

— R A₂ B₂ A₃ B₃ 423 n-C₃H₇

—

424 n-C₅H₁₁

—

425

—

426 CH₃

— 427 n-C₅H₁₁

— 428 n-C₃H₇

— 429 n-C₅H₁₁

— 430 CH₃

—

431 n-C₃H₇

—

432 n-C₃H₇

— 433 n-C₅H₁₁

— 434 n-C₃H₇

— 435 n-C₅H₁₁

— 436 n-C₃H₇

—

437 n-C₃H₇

—

438 n-C₅H₁₁

— 439 n-C₃H₇

— 440 nC₃H₇

—

441 n-C₅H₁₁

—

442 n-C₃H₇

— 443 n-C₃H₇

— 444 n-C₃H₇

—

445 n-C₅H₁₁

— 446 n-C₃H₇

— 447 CH₃

—

448 n-C₃H₇

—

449 n-C₅H₁₁

— 450 CH₃

— 451 CH₃

—

452 n-C₃H₇

—

453 n-C₅H₁₁

— 454 n-C₃H₇

—

455 n-C₃H₇

—

456 n-C₅H₁₁

— k = 1, m = 0, n = 1, R_(f) = CF₂CFHCF₃ R A₂ B₂ A₃ B₃ 457 CH₃

—

458 n-C₃H₇

— 459 CH₃

—

460 CH₃

— 461 CH₃

— 462 n-C₃H₇

—

—CO₂— 463 CH₃

—CO₂—

— 464 CH₃

—

465 CH₃

— 466 CH₃

—

467 CH₃

—

—CO₂— 468 CH₃

—CO₂—

— 469 CH₃

—

470 CH₃

— 471 CH₃

—

472 n-C₃H₇

—

—CO₂— 473 CH₃

—CO₂—

— 474 CH₃

—

R A₃ B₃ A₄ B₃ 475 CH₃

— 476 n-C₃H₇

—

477 CH₃

—

—CO₂— 478 CH₃

—

— 479 CH₃

—

480 CH₃

—

—CO₂— 481 CH₃

—CO₂—

— 482 CH₃

—

483 CH₃

— 484 CH₃

—

—CO₂— 485 n-C₃H₇

—CO₂—

— 486 CH₃

—

487 CH₃

— 488 CH₃

—

—CO₂— 489 n-C₃H₇

—CO₂—

— 490 CH₃

—

— 491 CH₃

—

492 CH₃

— 493 CH₃

—

— 494 CH₃

—

— R A₂ B₂ A₃ B₃ 495 n-C₃H₇

—

496 n-C₅H₁₁

—

497

—

498 CH₃

— 499 n-C₅H₁₁

— 500 n-C₃H₇

— 501 n-C₅H₁₁

— 502 CH₃

—

503 n-C₃H₇

—

504 n-C₃H₇

— 505 n-C₅H₁₁

— 506 n-C₃H₇

— 507 n-C₅H₁₁

— 508 n-C₃H₇

—

509 n-C₃H₇

—

510 n-C₅H₁₁

— 511 n-C₃H₇

— 512 n-C₃H₇

—

513 n-C₅H₁₁

—

514 n-C₃H₇

— 515 n-C₃H₇

— 516 n-C₃H₇

—

517 n-C₅H₁₁

— 518 n-C₃H₇

— 519 CH₃

—

520 n-C₃H₇

—

521 n-C₅H₁₁

— 522 CH₃

— 523 CH₃

—

524 n-C₃H₇

—

525 n-C₅H₁₁

— 526 n-C₃H₇

—

527 n-C₃H₇

—

528 n-C₃H₇

— 529 CH₃

—

530 n-C₃H₇

— 531 CH₃

—

532 CH₃

— 533 CH₃

— 534 n-C₃H₇

—

—CO₂— 535 CH₃

—CO₂—

— 536 CH₃

— 537 CH₃

—

538 CH₃

—

—CO₂— 539 CH₃

—CO₂—

— 540 CH₃

—

541 CH₃

— 542 CH₃

—

543 n-C₃H₇

—

—CO₂— 544 CH₃

—CO₂—

— 545 CH₃

—

R A₃ B₃ B₃ A₄ B₃ 546 CH₃

— 547 n-C₃H₇

—

548 CH₃

—

—CO₂— 549 CH₃

—

— 550 CH₃

—

551 CH₃

—

—CO₂— 552 CH₃

—CO₂—

— 553 CH₃

—

554 CH₃

— 555 CH₃

—

—CO₂— 556 n-C₃H₇

—CO₂—

— 557 CH₃

—

558 CH₃

— 559 CH₃

—

—CO₂— 560 n-C₃H₇

—CO₂—

— 561 CH₃

—

— 562 CH₃

—

563 CH₃

— 564 CH₃

—

— 565 CH₃

—

— R A₂ B₂ A₃ B₃ 566 n-C₃H₇

—

567 n-C₅H₁₁

—

568

—

569 CH₃

— 570 n-C₅H₁₁

— 571 n-C₃H₇

— 572 n-C₅H₁₁

— 573 CH₃

—

574 n-C₃H₇

—

575 n-C₃H₇

— 576 n-C₅H₁₁

— 577 n-C₃H₇

— 578 n-C₅H₁₁

— 579 n-C₃H₇

—

580 n-C₃H₇

—

581 n-C₅H₁₁

— 582 n-C₃H₇

— 583 n-C₃H₇

—

584 n-C₅H₁₁

—

585 n-C₃H₇

— 586 n-C₃H₇

— 587 n-C₃H₇

—

588 n-C₅H₁₁

— 589 n-C₃H₇

— 590 CH₃

—

591 n-C₃H₇

—

592 n-C₅H₁₁

— 593 CH₃

— 594 CH₃

—

595 n-C₃H₇

—

596 n-C₅H₁₁

— 597 n-C₃H₇

—

598 n-C₃H₇

—

599 n-C₅H₁₁

— k = m = n = 1, R_(f) = CF₃ R A₁ B₁ A₂ B₂ A₃ B₃ 600 CH₃

—

—

— 601 n-C₃H₇

—

—

— 602 CH₃

—

—

603 n-C₃H₇

—

—

604 CH₃

—

— 605 n-C₃H₇

—

— 606 CH₃

—

—

607 n-C₃H₇

—

— 611 CH₃

—

—

— 612 n-C₃H₇

—

—

— 613 CH₃

—

—

614 C₂H₅

—

615 C₂H₅

—

— 616 n-C₃H₇

—

— 617 CH₃

—

— 618 n-C₃H₇

—

— 622 CH₃

—

—

623 CH₃

—

—

— 624 n-C₃H₇

—

—

— 628 CH₃

—

—

629 CH₃

—

—

— 630 n-C₃H₇

—

—

— 631 CH₃

—

—

635 CH₃

—

—

— 636 CH₃

—

—

637 CH₃

—

— 638 CH₃

—

— 642 CH₃

—

—

— 643 n-C₃H₇

—

—

— 644 CH₃

—

—

645 CH₃

—

— 646 n-C₃H₇

—

— 647 n-C₃H₇

—

— 648 n-CH₃

—

— 652 CH₃

—

—

— 653 n-C₃H₇

—

—

— 654 n-C₃H₇

—

—

655 CH₃

—

— 656 CH₃

—

— 660 CH₃

—

—

— 661 n-C₃H₇

—

—

— 665 CH₃

—

—

666 CH₃

—

—

— 667 CH₃

—

—

— 668 CH₃

—

—

— 669 CH₃

—

—

— 670 CH₃

—

—

— 671 n-C₃H₇

—

—

— 672 CH₃

—

—

— 673 CH₃

—

—

— 674 CH₃

—

—

— 675 CH₃

—

—

— 676 CH₃

—

—

— 677 n-C₃H₇

—

—

— 678 CH₃

—

—

— 679 n-C₃H₇

—

—

— 680 CH₃

—

— 681 n-C₃H₇

—

— 682 CH₃

—

— 683 CH₃

—

—

— k = 0, m = n = 1, R_(f) = CF₃ 684 n-C₃H₇

—

—

685 n-C₅H₁₁

—

—

686 CH₃

—

— 687 n-C₅H₁₁

—

— 688 n-C₅H₁₁

—

— 689 n-C₃H₇

—

— 690 n-C₃H₇

—

—

691 CH₃

—

—

692 n-C₃H₇

—

— 693 n-C₅H₁₁

—

— 694 n-C₅H₁₁

—

— 695 n-C₃H₇

—

— 696 n-C₃H₇

—

—

697 n-C₅H₁₁

—

—

698 n-C₃H₇

—

— 699 n-C₃H₇

—

— 700 n-C₃H₇

—

— 701 n-C₅H₁₁

—

— 702 n-C₃H₇

—

—

703 n-C₃H₁₁

—

—

704 n-C₃H₇

—

— 705 n-C₃H₇

—

— 706 CH₃

—

— 707 n-C₅H₁₁

—

— 708 n-C₃H₇

—

—

709 CH₃

—

—

710 n-C₃H₇

—

— 711 n-C₅H₁₁

—

— 712 n-C₃H₇

—

— 713 n-C₃H₇

—

— 714 CH₃

—

—

715 n-C₃H₇

—

—

716 n-C₃H₇

—

— 717 n-C₅H₁₁

—

— 718 n-C₅H₁₁

—

— 719 CH₃

—

— 720 n-C₃H₇

—

—

721 n-C₅H₁₁

—

—

722 n-C₃H₇

—

— 723 n-C₅H₁₁

—

— 724 n-C₅H₁₁

—

— 725 CH₃

—

— 726 n-C₃H₇

—

—

727 n-C₅H₁₁

—

—

728 CH₃

—

— 729 n-C₃H₇

—

— 730 n-C₃H₇

—

— 731 CH₃

—

— 732 n-C₃H₇

—

—

733 n-C₅H₁₁

—

—

734 n-C₃H₇

—

— 735 n-C₃H₇

—

— 736 CH₃

—

— 737 n-C₃H₇

—

—

738 n-C₅H₁₁

—

—

739 n-C₃H₇

—

— k = m = n = 1, R_(f) = CF₂H 740 CH₃

—

—

— 741 n-C₃H₇

—

—

— 742 CH₃

—

—

743 n-C₃H₇

—

—

744 CH₃

—

— 745 n-C₃H₇

—

— 746 CH₃

—

— 747 n-C₃H₇

—

— 751 CH₃

—

—

— 752 n-C₃H₇

—

—

— 753 CH₃

—

—

754 n-C₃H₇

—

—

755 CH₃

—

— 756 n-C₃H₇

—

— 757 CH₃

—

— 758 n-C₃H₇

—

— 762 CH₃

—

—

763 CH₃

—

—

— 764 n-C₃H₇

—

—

— 768 CH₃

—

—

769 CH₃

—

—

— 770 n-C₃H₇

—

—

— 771 CH₃

—

—

775 CH₃

—

—

— 776 CH₃

—

—

777 CH₃

—

— 778 CH₃

—

— 782 CH₃

—

—

— 783 n-C₃H₇

—

—

— 784 CH₃

—

—

785 CH₃

—

— 786 n C₃H₇

—

— 787 n-C₃H₇

—

— 789 n-CH₃

—

— 793 CH₃

—

—

— 794 n-C₃H₇

—

—

— 795 n-C₃H₇

—

—

796 CH₃

—

— 797 CH₃

—

— 801 CH₃

—

—

— 802 n-C₃H₇

—

—

— 806 CH₃

—

—

807 CH₃

—

—

— 808 CH₃

—

—

— 809 CH₃

—

—

— 810 CH₃

—

—

— 811 CH₃

—

—

— 812 n-C₃H₇

—

—

— 813 CH₃

—

—

— 814 CH₃

—

—

— 815 CH₃

—

—

— 816 CH₃

—

—

— 817 CH₃

—

—

— 818 n-C₃H₇

—

—

— 819 CH₃

—

—

— 820 n-C₃H₇

—

—

— 821 CH₃

— 822 n-C₃H₇

— 823 CH₃

— 824 CH₃

—

—

— k = 0, m = n = 1, R_(f) = CF₂H 825 n-C₃H₇

—

—

826 n-C₅H₁₁

—

—

827 CH₃

—

— 828 n-C₅H₁₁

—

— 829 n-C₅H₁₁

—

— 830 n-C₃H₇

—

— 831 n-C₃H₇

—

—

832 CH₃

—

—

833 n-C₃H₇

—

— 834 n-C₅H₁₁

—

— 835 n-C₅H₁₁

—

— 836 n-C₃H₇

—

— 837 n-C₃H₇

—

—

838 n-C₅H₁₁

—

—

839 n-C₃H₇

—

— 840 n-C₃H₇

—

— 841 n-C₃H₇

—

— 842 n-C₅H₁₁

—

— 843 n-C₃H₇

—

—

844 n-C₅H₁₁

—

—

845 n-C₃H₇

—

— 846 n-C₃H₇

—

— 847 CH₃

—

— 848 n-C₅H₁₁

—

— 849 n-C₃H₇

—

—

850 CH₃

—

—

851 n-C₃H₇

—

— 852 n-C₅H₁₁

—

— 853 n-C₃H₇

—

— 854 n-C₃H₇

—

— 855 CH₃

—

—

856 n-C₃H₇

—

—

857 n-C₃H₇

—

— 858 n-C₅H₁₁

—

— 859 n-C₅H₁₁

—

— 860 CH₃

—

— 861 n-C₃H₇

—

—

862 n-C₅H₁₁

—

—

863 n-C₃H₇

—

— 864 n-C₅H₁₁

—

— 865 n-C₅H₁₁

—

— 866 CH₃

—

— 867 n-C₃H₇

—

—

868 n-C₅H₁₁

—

—

869 CH₃

—

— 870 n-C₃H₇

—

— 871 n-C₃H₇

—

— 872 CH₃

—

— 873 n-C₃H₇

—

—

874 n-C₅H₁₁

—

—

875 n-C₃H₇

—

— 876 n-C₃H₇

—

— 877 CH₃

—

— 878 n-C₃H₇

—

—

879 n-C₅H₁₁

—

—

880 n-C₃H₇

—

— k = m = n = 1, R_(f) CH₂CF₃ 881 CH₃

—

—

882 CH₃

—

—

883 n-C₃H₇

—

— 884 CH₃

—

— 885 n-C₃H₇

—

— 886 CH₃

—

—

—CO₂— 887 n-C₃H₇

—

—CO₂—

— 888 CH₃

—CO₂—

—

— 889 CH₃

—

—

890 CH₃

—

— 891 n-C₃H₇

—

— 892 CH₃

—

— 893 n-C₃H₇

—

— 894 CH₃

—

—

—CO₂— 895 n-C₃H₇

—

—CO₂—

— 896 CH₃

—CO₂—

—

— 897 CH₃

—

—

898 CH₃

—

—

—CO₂— 899 CH₃

—

—CO₂—

— 900 CH₃

—CO₂—

—CO₂—

— 901 CH₃

—

—

902 CH₃

—

—

903 CH₃

—

—

—CO₂— 904 CH₃

—

—CO₂—

— 905 CH₃ —

—CO₂—

—

906 CH₃

—

—

— 907 CH₃

—

—

908 CH₃

—

— 909 CH₃

—

— 910 CH₃

—

—

—CO₂— 911 n-C₃H₇

—

—CO₂—

— 912 CH₃

—CO₂—

—

— 913 CH₃

—

—

914 CH₃

—

— 915 n-C₃H₇

—

— 916 n-C₃H₇

—

— 917 n-CH₃

—

— 918 CH₃

—

—

—CO₂— 919 n-C₃H₇

—

—CO₂— — 920 CH₃

—CO₂—

—

— 921 n-C₃H₇

—

—

922 CH₃

—

— 923 CH₃

—

— 924 CH₃

—

—

—CO₂— 925 CH₃

—

—CO₂—

— 926 CH₃

—CO₂—

—

— 927 CH₃

—

—CO₂— 928 CH₃

—

—CO₂—

— 929 CH₃

—CO₂—

—CO₂—

— 930 CH₃

—

—

931 CH₃

—

—

— 932 CH₃

—

—

— 933 CH₃

—

—

— 934 CH₃

—

—

— 935 CH₃

—

—

— 936 n-C₃H₇

—

—

— 937 CH₃

—

—

— 938 CH₃

—

—

— 939 CH₃

—

—

— 940 CH₃

—

—

— 941 CH₃

—

—

— 942 n-C₃H₇

—

—

— 943 CH₃

—

—

— 944 n-C₃H₇

—

—

— 945 CH₃

—

— 946 n-C₃H₇

—

— 947 CH₃

—

— 948 CH₃

—

—

— 949 n-C₃H₇

—

—

950 n-C₃H₇

—

—

951 CH₃

—

— 952 n-C₅H₁₁

—

— 953 n-C₅H₁₁

—

— 954 n-C₃H₇

—

— 955 n-C₃H₇

—

—

956 CH₃

—

—

957 n-C₃H₇

—

— 958 n-C₅H₁₁

—

— 959 n-C₅H₁₁

—

— 960 n-C₃H₇

—

— 961 n-C₃H₇

—

—

962 n-C₅H₁₁

—

—

963 n-C₃H₇

—

— 964 n-C₃H₇

—

— 965 n-C₃H₇

—

— 966 n-C₅H₁₁

—

— 967 n-C₃H₇

—

—

968 n-C₅H₁₁

—

—

969 n-C₃H₇

—

— 970 n-C₃H₇

—

— 971 CH₃

—

— 972 n-C₅H₁₁

—

— 973 n-C₃H₇

—

—

974 CH₃

—

—

975 n-C₃H₇

—

— 976 n-C₅H₁₁

—

— 977 n-C₃H₇

—

— 978 n-C₃H₇

—

— 979 CH₃

—

—

980 n-C₃H₇

—

—

981 n-C₃H₇

—

— 982 n-C₅H₁₁

—

— 983 n-C₅H₁₁

—

— 984 CH₃

—

— 985 n-C₃H₇

—

—

986 n-C₅H₁₁

—

—

987 n-C₃H₇

—

— 988 n-C₅H₁₁

—

— 989 n-C₅H₁₁

—

— 990 CH₃

—

— 991 n-C₃H₇

—

—

992 n-C₅H₁₁

—

—

993 CH₃

—

— 994 n-C₃H₇

—

— 995 n-C₃H₇

—

— 996 CH₃

—

— 997 n-C₃H₇

—

—

998 n-C₅H₁₁

—

—

999 n-C₃H₇

—

— 1000 n-C₃H₇

—

— 1001 CH₃

—

— 1002 n-C₃H₇

—

—

1003 n-C₅H₁₁

—

—

1004 n-C₃H₇

—

— m = n = 1, CF₂CFHCF₃ 1005 CH₃

—

—

1006 CH₃

—

— 1007 n-C₃H₇

—

— 1008 CH₃

—

— 1009 n-C₃H₇

—

— 1010 CH₃

—

—

—CO₂— 1011 n-C₃H₇

—

—CO₂—

— 1012 CH₃

—CO₂—

—

— 1013 CH₃

—

—

1014 CH₃

—

— 1015 n-C₃H₇

—

— 1016 CH₃

—

— 1017 n-C₃H₇

—

— 1018 CH₃

—

—

—CO₂— 1019 n-C₃H₇

—

—CO₂—

— 1020 CH₃

—CO₂—

—

— 1021 CH₃

—

—

1022 CH₃

—

—CO₂— 1023 CH₃

—

—CO₂—

— 1024 CH₃

—CO₂—

—CO₂—

— 1025 CH₃

—

—

1026 CH₃

—

—

1027 CH₃

—

—

—CO₂— 1028 CH₃

—

—CO₂—

— 1029 CH₃

—CO₂—

—

— 1030 CH₃

—

—

— 1031 CH₃

—

—

1032 CH₃

—

— 1033 CH₃

—

— 1034 CH₃

—

—

—CO₂— 1035 n-C₃H₇

—

—CO₂—

— 1036 CH₃

—CO₂—

—

— 1037 CH₃

—

—

1038 CH₃

—

— 1039 n-C₃H₇

—

— 1040 n-C₃H₇

—

— 1041 n-CH₃

—

— 1042 CH₃

—

—

—CO₂— 1043 n-C₃H₇

—

—CO₂—

— 1044 CH₃

—CO₂—

—

— 1045 n-C₃H₇

—

—

1046 CH₃

—

— 1047 CH₃

—

— 1048 CH₃

—

—

—CO₂— 1049 CH₃

—

—CO₂—

— 1050 CH₃

—CO₂—

—

— 1051 CH₃

—

—CO₂— 1052 CH₃

—

—CO₂—

— 1053 CH₃

—CO₂—

—CO₂—

— 1054 CH₃

—

—

1055 CH₃

—

—

— 1056 CH₃

—

—

— 1057 CH₃

—

—

— 1058 CH₃

—

—

— 1059 CH₃

—

—

— 1060 n-C₃H₇

—

—

— 1061 CH₃

—

—

— 1062 CH₃

—

—

— 1063 CH₃

—

—

— 1064 CH₃

—

—

— 1065 CH₃

—

—

— 1066 n-C₃H₇

—

—

— 1067 CH₃

—

—

— 1068 n-C₃H₇

—

—

— 1069 CH₃

—

— 1070 n-C₃H₇

—

— 1071 CH₃

—

— 1072 CH₃

—

—

— 1073 n-C₃H₇

—

—

1074 n-C₅H₁₁

—

—

1075 CH₃

—

— 1076 n-C₅H₁₁

—

— 1077 n-C₅H₁₁

—

— 1078 n-C₃H_(7—)

—

— 1079 n-C₃H₇

—

—

1080 CH₃

—

—

1081 n-C₃H₇

—

— 1082 n-C₅H₁₁

—

— 1083 n-C₅H₁₁

—

— 1084 n-C₃H₇

—

— 1085 n-C₃H₇

—

—

1086 n-C₅H₁₁

—

—

1087 n-C₃H₇

—

— 1088 n-C₃H₇

—

— 1089 n-C₃H₇

—

— 1090 n-C₅H₁₁

—

— 1091 n-C₃H₇

—

—

1092 n-C₅H₁₁

—

—

1093 n-C₃H₇

—

— 1094 n-C₃H₇

—

— 1095 CH₃

—

— 1096 n-C₅H₁₁

—

— 1097 n-C₃H₇

—

—

1098 CH₃

—

—

1099 n-C₃H₇

—

— 1100 n-C₅H₁₁

—

— 1101 n-C₃H₇

—

— 1102 n-C₃H₇

—

— 1103 CH₃

—

—

1104 n-C₃H₇

—

—

1105 n-C₃H₇

—

— 1106 n-C₅H₁₁

—

— 1107 n-C₅H₁₁

—

— 1108 CH₃

—

— 1109 n-C₃H₇

—

—

1110 n-C₅H₁₁

—

—

1111 n-C₃H₇

—

— 1112 n-C₅H₁₁

—

— 1113 n-C₅H₁₁

—

— 1114 CH₃

—

— 1115 n-C₃H₇

—

—

1116 n-C₅H₁₁

—

—

1117 CH₃

—

— 1118 n-C₃H₇

—

— 1119 n-C₃H₇

—

— 1120 CH₃

—

— 1121 n-C₃H₇

—

—

1122 n-C₅H₁₁

—

—

1123 n-C₃H₇

—

— 1124 n-C₃H₇

—

— 1125 CH₃

—

— 1126 n-C₃H₇

—

—

1127 n-C₅H₁₁

—

—

1128 n-C₃H₇

—

— = m = n = 1, = CH₂CF₂CF₃ 1129 CH₃

—

—

1130 CH₃

—

— 1131 n-C₃H₇

—

— 1132 CH₃

—

— 1133 n-C₃H₇

—

— 1134 CH₃

—

—

—CO₂— 1135 n-C₃H₇

—

—CO₂—

— 1136 CH₃

—CO₂—

—

— 1137 CH₃

—

—

1138 CH₃

—

— 1139 n-C₃H₇

—

— 1140 CH₃

—

— 1141 n-C₃H₇

—

— 1142 CH₃

—

—

—CO₂— 1143 n-C₃H₇

—

—CO₂—

— 1144 CH₃

—CO₂—

—

— 1145 CH₃

—

—

1146 CH₃

—

—CO₂— 1147 CH₃

—

—CO₂—

— 1148 CH₃

—CO₂—

—CO₂—

— 1149 CH₃

—

—

1150 CH₃

—

—

1151 CH₃

—

—

—CO₂— 1152 CH₃

—

—CO₂—

— 1153 CH₃

—CO₂—

—

— 1154 CH₃

—

—

— 1155 CH₃

—

—

1156 CH₃

—

— 1157 CH₃

—

— 1158 CH₃

—

—

—CO₂— 1159 n-C₃H₇

—

—CO₂—

— 1160 CH₃

—CO₂—

—

— 1161 CH₃

—

—

1162 CH₃

—

— 1163 n-C₃H₇

—

— 1164 n-C₃H₇

—

— 1165 n-CH₃

—

— 1166 CH₃

—

—

—CO₂— 1167 n-C₃H₇

—

—CO₂—

— = m = n = 1, = CH₂CF₃ 1168 CH₃

—CO₂—

—

— 1169 n-C₃H₇

—

—

1170 CH₃

—

— 1171 CH₃

—

— 1172 CH₃

—

—

—CO₂— 1173 CH₃

—

—CO₂—

— 1174 CH₃

—CO₂—

—

— 1175 CH₃

—

—CO₂— 1176 CH₃

—

—CO₂—

— 1177 CH₃

—CO₂—

—CO₂—

— 1178 CH₃

—

—

1179 CH₃

—

—

— 1180 CH₃

—

—

— 1181 CH₃

—

—

— 1182 CH₃

—

—

— 1183 CH₃

—

—

— K = 0, m = n = 1, R_(f) = CH₂CF₂CF₃ 1184 n-C₃H₇

—

—

— 1185 CH₃

—

—

— 1186 CH₃

—

—

— 1187 CH₃

—

—

— 1188 CH₃

—

—

— 1189 CH₃

—

—

— 1190 n-C₃H₇

—

—

— 1191 CH₃

—

—

— 1192 n-C₃H₇

—

—

— 1193 CH₃

—

— 1194 n-C₃H₇

—

— 1195 CH₃

—

— 1196 CH₃

—

—

— 1197 n-C₃H₇

—

—

1198 n-C₅H₁₁

—

—

1199 CH₃

—

— 1200 n-C₅H₁₁

—

— 1201 n-C₅H₁₁

—

— 1202 n-C₃H₇

—

— 1203 n-C₃H₇

—

—

1204 CH₃

—

—

1205 n-C₃H₇

—

— 1206 n-C₅H₁₁

—

— 1207 n-C₅H₁₁

—

— 1208 n-C₃H₇

—

— 1209 n-C₃H₇

—

—

1210 n-C₅H₁₁

—

—

1211 n-C₃H₇

—

— 1212 n-C₃H₇

—

— 1213 n-C₃H₇

—

— 1214 n-C₅H₁₁

—

— 1215 n-C₃H₇

—

—

1216 n-C₅H₁₁

—

—

1217 n-C₃H₇

—

— 1218 n-C₃H₇

—

— 1219 CH₃

—

— 1220 n-C₅H₁₁

—

— 1221 n-C₃H₇

—

—

1222 CH₃

—

—

1223 n-C₃H₇

—

— 1224 n-C₅H₁₁

—

— 1225 n-C₃H₇

—

— 1226 n-C₃H_(7 —)

—

— 1227 CH₃

—

—

1228 n-C₃H₇

—

—

1229 n-C₃H₇

—

— 1230 n-C₅H₁₁

—

— 1231 n-C₅H₁₁

—

— 1232 CH₃

—

— 1233 n-C₃H₇

—

—

1234 n-C₅H₁₁

—

—

1235 n-C₃H₇

—

— 1236 n-C₅H₁₁

—

— 1237 n-C₅H₁₁

—

— 1238 CH₃

—

— 1239 nC₃H₇

—

—

1240 n-C₅H₁₁

—

—

1241 CH₃

—

— 1242 n-C₃H₇

—

— 1243 n-C₇H₇

—

— 1244 CH₃

—

— 1245 n-C₃H₇

—

—

1246 n-C₅H₁₁

—

—

1247 n-C₃H₇

—

— 1248 n-C₃H₇

—

— 1249 CH₃

—

— 1250 n-C₃H₇

—

—

1251 n-C₅H₁₁

—

—

1252 n-C₃H₇

—

—

Example 6 (Use Example 1)

A nematic liquid cystal composition (hereinaftlrxeferred to as liquid crystal composition A1) containing of the components: 4-(trans-4-propylcyclohexy) benzonitrfle 24% by weight, 4-(trans-4-pentylcyclohexyl) benzonitrile 36% by weight, 4-(trans-4-heptylcyclohexyl) benzonitrile 25% by weight and 4-(trans-4-propylphenyl) benzonitrile 15% by weight has the following characteristics:

Clearing point (T_(NI)): 71.7° C., threshold voltage at cell thickness of 9 μ(V_(th)); 1.78V, Δε: 11.0, Δn: 0.137, viscosity at 20° C.: 26.3 mPa.s.

85% by weight of the liquid crystal composition A1 was mixed with 15% by weight of 2,6-difluoro-4-(trans-4-(trans-4-methoxymethylcyclohexyl) (cyclohexyl) trifluoromethoxybenzene (Compound No. 153) obtained in Example 1 to prepare a liquid crystal composition B1. The physical properties of the composition B1 was determined as follows:

T_(NI): 71.0° C., V_(th): 1.57V, Δε: 12.3, Δn: 0.129, η20: 32.2 mPa.s

This composition was allowed to stand in a freezer at −20° C. for 30 days, but both deposition of crystals and smectic phase were not observed.

Example 7 (Use Example 2)

Liquid crystal composition B2 was prepared in the same manner as Example 6 except that 2,6-difluoro-4-(4-(trans-4-methoxymethylcyclohexyl)-2,6-difluorophenyl) trifluoromethoxybenzene (Compound No. 187) obtained in Example 2 was mixed with A1 in place of Compound No. 153. The physical properties of the composition B2 was determined as follows:

T_(NI): 63.0° C., V_(th): 1.49V, Δε: 14.1, Δn: 0.132, η20: 35.5 mPa.s

Example 8 (Use Example 3)

Liquid crystal composition B3 was prepared in the same manner as Example 6 except that 2,6-difluoro-4-(4-(trans-4-pentylcyclohexyl) methoxyphenyl) trifluoromethoxybenzene (Compound No. 239) obtained in Example 3 was mixed with A1 in place of Compound No. 153. The physical properties of the composition B3 was determined as follows:

T_(NI): 71.4° C., V: 1.73V, Δε: 10.9, Δn: 0.135, η20: 37.6 mPa.s

Example 9 (Use Example 4)

Liquid crystal composition B4 was prepared in the same manner as Example 6 except that 2,6-difluoro-4-(trans-4-(trans-4-methoxymethylcyclohexyl) cyclohexyl) difluoromethoxybenzene (Compound No. 269) obtained in Example 4 was mixed with A1 in place of Compound No. 153. The physical properties of the composition B4 was determined as follows:

T_(NI): 72.4° C., V_(th): 1.69V, Δε: 12.2, Δn: 0.131, η20: 31.6 mPa.s

Further, the compositions prepared by Example 7 to 9 were allowed to stand in a freezer at −20 ° C. for 30 days, but both deposition of crystals and smectic phase were not observed from all the compositions.

Comparative Example 1

Physical properties of the compounds of the present invention were determined based on the data in the above-mentioned Examples and were summarized in Table 2.

Furthermore, compounds (50) to (53) which are identical to compounds expressed by the above-mentioned formulae (10), (12), (13) and (14) wherein R is specified as propyl group were practically synthesized and their physical properties were determined in the same manner as above-mentioned Examples. Amongst of the respective physical properties, Δε and η20 are shown by extrapolated values. [Table 2]

TABLE 2 Compounds T_(NI) (° C.) Δ_(E) η₂₀ (mPa·s) Vth (V) Liquid Crystal Composition A1 71.1 11.0 27.0 1.78

No. 153 71.0 19.7 65.6 1.57

No. 187 63.0 31.7 88.2 1.49

No. 269 72.4 19.0 62.2 1.69

(50) 66.7 19.7 58.3 1.59

(51) 72.0 15.0 46.2 1.70

(52) 72.0 15.0 61.7 1.66

(53) 74.0 11.0 47.2 1.72

As is shown in Table 2, it is apparent that the compounds of the present invention exhibit high dielectric anisotropy (Δε) valueas.

For instance, Compounds No. 153 and 269 have as higher Δε values of 19.7 and 19.0, respectively, while the known reference compounds (51) and (53) wherein propyl group is only replaced from methoxymethyl group have the values of 15.0 and 11.0, respectively. Further, Compound No. 187 was found to have as very high Δε value of 31.7. Although the compounds of the present invention exhibit somewhat higher viscosity values than those of the reference compounds, the compounds are found to have capability so that they let liquid crystal cells drive at lower threshold voltage than those of the reference compounds due to their very high Δε values.

Furthermore, it was found that T_(NI) values of liquid crystals, which were obtained from the mother liquid crystal by adding thereto the compounds of the invention, were only either somewhat increased (No. 269) or unchanged (No. 153, 187).

From these results, it was found that the compounds of the present invention could contribute to lower threshold voltages of mother liquid crystals without lowering clearing points of liquid crystal compositions, and also recognized that the compounds have a superior miscibility at a low temperature as described before.

Thus, by using the compounds of the present invention, liquid crystal compositions having properties such as (1) lowering threshold voltages without lowering clearing points of mother liquid crystals and (2) being superior in miscibility, especially in miscibility at a low temperature can be first prepared. And, by using the compositions, liquid crystal display elements having properties of high response speed and low voltage drive-ability can be provided

EFFECT OF THE INVENTION

As described above, the compounds of the present invention expressed by the general formula (1) are the ones having a very high dielectric anisotropy value, being stable against outer environment and being superior in miscibility with other liquid crystal compounds, especially at a low temperature.

Thus, by using the liquid crystalline compounds of the present invention as constitutional components of liquid crystal compositions, there can be provided liquid crystal compositions and display elements having properties of high response speed and low voltage drive-ability. 

What is claimed is:
 1. A fluoroalkoxybenzene derivative expressed by the general formula (1)

wherein A₁, A₂ and A₃ each independently denote trans-1,4-cyclohexylene, 1,4-phenylene in which one or more hydrogen atoms may optionally be substituted with a fluorine atom(s), 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or 1-sila-1,4-cyclohexylene; B₁, B₂ and B₃ each independently denote a single bond, 1,2- ethylene, 1,2-cethenylene, 1,2-ethynylene, oxymethylene, methyleneoxy, carbonyloxy or 1,4-butylene group; R denotes an alkyl croup having 1 to 15 carbon atoms optionally substitutable with a halogen atom(s), wherein one or more non-adjacent ethylene groups may be replaced by 1,2-ethenylene group(s); RE denotes a fluoroalLyl group having 1 to 3 carbon atoms substitutable with two or more fluorine atoms; k, m, and n each independentiy denote 0 or 1, with the proviso that when k=0 is a case, then one of B₁, B₂ and B₃ is a methyleneoxy or oxymethylene bond, that when k=1 and Rf denotes CF₃ or CF₂H, then both B₁ and B₃, or both B₂ and B₃ are never carbonyloxy groups, that when m+n=2 is a case, then both A₁ and A₃, or both A₂ and A₃ are not 1,4-phenylene at the same time, respectively, and further when both A₁ and A₃, or both A₂ and A₃ are trans-1, 4-cyclohexylene or 1,4-phenylene and both B₁ and B₃, or both B₂ and B3 are all single bonds, then Rf is never C₂F₅, CH₂CF₃ or CH₂CF₂CF₃, that when m+n=1 is a case, both A₁ and A₃, or both A₂ and A₃ are trans-1,4-cyclohexylene at the same time, respectively, B₁ or B₂ is a single bond and B₃ is 1,2-ethylene, then Rf is never CH₂CF₂CF₃, and that when m+n=0 is a case and A₃ is 1-sila-1,4-cyclohexylene, then B3 is never methyleneoxy group.
 2. A compound according to claim 1 wherein k=1.
 3. A compound according to claim 1 wherein one of B₁, B₂ or B₃ is a methyleneoxy or oxymethylene bond.
 4. A compound according to claim 2 wherein m=0, n=1, A₂ and A₃ are 1, 4-cyclohexylene, and B₂ and B₃ are single bonds.
 5. A compound according to claim 2 wherein m=0, n=1, A₂ is 1, 4-cyclohexylene, A₃ is 1, 4-cyclohexylene optionally substitutable with a fluorine atom(s), and B₂ and B₃ are both single bonds.
 6. A compound according to claim 2 wherein m+n=1, A₁ or A₂ and A₃ are both trans-1, 4-cyclohexylenes, B₁ or B₂ is 1, 2-ethylene, and B₃ is a single bond.
 7. A compound according to claim 2 wherein m+n=1, A₁ or A₂ and A₃ are both trans-1, 4-cyclohexylenes, B₁ or B₂ is a single bond, and B₃ is 1,2-ethylene.
 8. A compound according to claim 2 wherein m=n=1, and A₁ and A₂ are both trans-1, 4-cyclohexylenes.
 9. A compound according to claim 8 wherein m=n=1, A₁ and A₂ are both trans-1, 4-cyclohexylenes, A₃ is 1, 4-phenylene one or two hydrogen atoms of which may be optionally substituted with a fluorine atom(s), B₁ and B₃ are single bonds, and B₂ is 1,2-ethylene.
 10. A liquid crystal composition comprising at least one liquid crystalline compound defined in any one of claims 1 to
 9. 11. A liquid crystal composition comprising, as a first component, at least one liquid crystalline compound defined in any one of claims 1 to 9, and as a second component, at least one compound selected from the group of compounds expressed by any one of general formulae (2), (3), and (4)

wherein R₃ denotes an alkyl group having 1 to 10 carbon atom(s) in which alkyl group any non-adjacent methylene group may be replaced by an oxygen atom or —CH═CH—, and any hydrogen atom may be replaced by a fluorine atom; Y1 denotes a fluorine atom, a chlorine atom, OCF₃, OCF₂H, CF₃, CF₂H, CFH₂, OCF₂CF₂H or OCF₂CFHCF₃; L₁ and L₂ each independently denote a hydrogen atom or a fluorine atom; Z, and Z₂ each independently denote 1,2-ethylene group, 1,4-butylene group, —COO—, —CF₂O—, —OCF₂—, —CH═CH—, or a single bond; B denotes trans-1,4-cyclohexylene, 1,3-dioxane-2,5-diyl or 1,4-phenylene any hydrogen atom of which may be replaced by a fluorine atom; and C denotes trans-1,4-cyclohexylene or 1,4-phenylene any hydrogen atom of which may be replaced by a fluorine atom.
 12. A liquid crystal composition comprising, as a first component, at least one liquid crystalline compound defined in any one of claims 1 to 9, and as a second component, at least one compound selected from a group of compounds expressed by any one general formulae (5) and (6)

wherein R₄ and R₅ each independently denote an alkyl group having 1 to 10 carbon atoms in which alkyl group any non-adjacent methylene group may be replaced by an oxygen atom or —CH═CH— and any hydrogen atom of which may be replaced by a fluorine atom; Y₂ denotes —CN group or —C═C—CN group; E denotes trans-1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; G denotes trans-1,4-cyclohexylene, 1,4-phenylene any hydrogen atom of which may be replaced by a fluorine atom or pyrirnidine-2,5-diyl; H denotes trans-1,4-cyclohexylene or 1,4-phenylene; Z₃ denotes 1,2-ethylene group, —COO— or a single bond; L₃, L₄ and L₅ each independently denote a hydrogen atom or fluorine atom, and b, c and d each independently denote 0 or
 1. 13. A liquid crystal composition according to claim 10 wherein the liquid crystal composition further comprises one or more optically active compounds.
 14. A liquid crystal display element comprising a liquid crystal composition defined in claim
 10. 15. A liquid crystal composition comprising, as a first component, at least one liquid crystalline compound defined in any one of claims 1 to 9, as a second component, at least one compound selected from the group of compounds expressed by any one of general formulae (2), (3), and (4), and as a third component, at least one compound selected from the group of compounds expressed by any one of the general formulae (7), (8) and (9)

wherein R₃ denotes an alkyl group having 1 to 10 carbon atom(s) in which alkyl group any non-adjacent methylene group may be replaced by an oxygen atom or —CH═CH—, and any hydrogen atom may be replaced by a fluorine atom; Y₁ denotes a fluorine atom, a chlorine atom, OCF₃, OCF₂H, CF₃, CF₂H, CFH₂, OCF₂CF₂H or OCF₂CFHCF₃; L₁ and L₂ each independently denote a hydrogen atom or a fluorine atom; Z₁ and Z₂ each independently denote 1,2-ethylene group, 1,4-butylene group, —COO—, —CF₂O—, —OCF₂—, —CH═CH—, or a single bond; B denotes trans-1,4-cyclohexylene, 1,3-dioxane-2,5-diyl or 1,4-phenylene any hydrogen atom of which may be replaced by a fluorine atom; and C denotes trans-1,4-cyclohexylene or 1,4-phenylene any hydrogen atom of which may be replaced by a fluorine atom,

wherein R₆ and R₇ each independently denote an alkyl group having 1 to 10 carbon atoms in which alkyl group any non-adjacent methylene group may be replaced by an oxygen atom or —CH═CH— and any hydrogen atom of which may be replaced by a fluorine atom; I, J and K each independently denote trans-1,4,-cyclohexylene, pyrimidine-2,5-diyl or 1 ,4-phenylene any hydrogen atom of which may be replaced by a fluorine atom; and Z₄ and Z₅ each independently denote —C≡C—, —COO—, —CH₂CH₂—, —CH═CH— or a single bond.
 16. A liquid crystal composition comprising, as a first component, at least one liquid crystalline compound defined in any one of claims 1 to 9, as a second component, at least one compound selected from the group of compounds expressed by any one of general formulae (5) and (6); and as a third component, at least one compound selected from the group of compounds expressed by any one of the general formulae (7), (8) and (9)

wherein R₄ and R₅ each independently denote an alkyl group having 1 to 10 carbon atoms in which alkyl group any non-adjacent methylene group may be replaced by an oxygen atom or —CH═CH— and any hydrogen atom of which may be replaced by a fluorine atom; Y₂ denotes —CN group or —C—C—CN group; E denotes trans-1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; G denotes trans-1,4-cyclohexylene, 1,4-phenylene any hydrogen atom of which may be replaced by a fluorine atom or pyrimidine-2,5-diyl; H denotes trans-1, 4-cyclohexylene or 1,4-phenylene; Z₃ denotes 1,2-ethylene group, —COO— or a single bond; L₃, L₄ and L₅ each independently denote a hydrogen atom or fluorine atom, and b, c and d each independently denote 0 or 1, R₆IZ₄JZ₅—R₇  (7) R₆IZ₄JZ₅KR₇  (9)

wherein R₆ and R₇ each independently denote an alkyl group having 1 to 10 carbon atoms in which alkyl group any non-adjacent methylene group may be replaced by an oxygen atom or —CH═CH— and any hydrogen atom of which may be replaced by a fluorine atom; I, J and K each independently denote trans-1,4,-cyclohexylene, pyrimidine-2,5-diyl or 1,4-phenylene any hydrogen atom of which may be replaced by a fluorine atom; and Z₄ and Z₅ each independently denote —C≡—C—, —COO—, —CH₂CH₂—, —CH═CH— or a single bond.
 17. A liquid crystal composition comprising, as a first component, at least one liquid crystalline compound defined in any one of claims 1 to 9, as a second component, at least one compound selected from the group of compounds expressed by any one of general formulae (2), (3), and (4), as a third component, at least one compound selected from the group of compounds expressed by any one of the general formulae (5) and (6), and as a fourth component, at least one compound selected from the group of compounds expressed by any one of the general formulae (7), (8) and (9)

wherein R₃ denotes an alkyl group having 1 to 10 carbon atom(s) in which alkyl group any non-adjacent methylene group may be replaced by an oxygen atom or —CH═CH—, and any hydrogen atom may be replaced by a fluorine atom; Y₁ denotes a fluorine atom, a chlorine atom, OCF₃, OCF₂H, CF₃, CF₂H, CFH2, OCF₂CF₂H or OCF₂CFHCF₃; L₁ and L₂ each independently denote a hydrogen atom or a fluorine atom; Z₁ and Z₂ each independently denote 1,2-ethylene group, 1,4-butylene group, —COO—, —CF₂O—, —OCF₂—, —CH═CH—, or a single bond; B denotes trans-1,4-cyclohexylene, 1,3-dioxane-2,5-diyl or 1,4-phenylene any hydrogen atom of which may be replaced by a fluorine atom; and C denotes trans-1,4-cyclohexylene or 1,4-phenylene any hydrogen atom of which may be replaced by a fluorine atom,

wherein R₄ and R₅ each independently denote an alkyl group having 1 to 10 carbon atoms in which alkl group any non-adjacent methylene group may be replaced by an oxygen atom or —CH═CH— and any hydrogen atom of which may be replaced by a fluorine atom; Y₂ denotes —CN group or —C≡C—CN group; E denotes trans-1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; G denotes trans-1,4-cyclohexylene, 1,4-phenylene any hydrogen atom ofwhich may be replaced by a fluorine atom or pyrimidine-2,5-diyl; H denotes trans-1,4-cyclohexylene or 1,4-phenylene; Z₃ denotes 1,2-ethylene group, —COO— or a single bond; L₃, L₄ and L₅ each independently denote a hydrogen atom or fluorine atom, and b, c and d each independently denote 0 or 1,

wherein R₆ and R₇ each independently denote an alkyl group having 1 to 10 carbon atoms in which alkyl group any non-adjacent methylene group may be replaced by an oxygen atom or —CH═CH— and any hydrogen atom of which may be replaced by a fluorine atom; I, J and K each independently denote trans-1,4,-cyclohexylene, pyrimnidine-2,5-diyl or 1,4-phenylene any hydrogen atom of which may be replaced by a fluorine atom; and Z₄ and Z₅ each independently denote —C≡C—, —COO—, —CH₂CH₂—, —CH═CH— or a single bond. 